115268-43-4

Usage

Uses

As the provided materials do not specify any particular applications for (1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[1(S)-hydroxy-3-[4-methyl-3,6-dihydro-2H-pyran-2(S)-yl]-2(E)-propenyl]-3-methyl-5-methylene-9,13,22-trioxatricyclo[16.3.1.0(8,10)]docosa-15,19-dien-14-one, it is not possible to list its uses based on the given information. However, given its complex structure and potential for biological or pharmaceutical relevance, it may be worth investigating its potential applications in various industries, such as:
Used in Pharmaceutical Industry:
(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[1(S)-hydroxy-3-[4-methyl-3,6-dihydro-2H-pyran-2(S)-yl]-2(E)-propenyl]-3-methyl-5-methylene-9,13,22-trioxatricyclo[16.3.1.0(8,10)]docosa-15,19-dien-14-one could be used as a pharmaceutical agent for [specific application reason], given its complex structure and potential for biological activity.
Used in Chemical Research Industry:
(1R,3S,7S,8S,10S,12S,18R)-7-Hydroxy-12-[1(S)-hydroxy-3-[4-methyl-3,6-dihydro-2H-pyran-2(S)-yl]-2(E)-propenyl]-3-methyl-5-methylene-9,13,22-trioxatricyclo[16.3.1.0(8,10)]docosa-15,19-dien-14-one could be used as a research tool in chemical research for [specific research purpose], such as studying its synthesis, properties, or interactions with other molecules.

Upstream product

• 856410-42-9 (E)-(S)-1-[(S)-2-(4-Methoxy-phenyl)-[1,3]dioxan-4-yl]-3-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-prop-2-en-1-ol 
• 856410-64-5 (2S,6R)-6-(3,3-Dibromo-allyl)-2-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-3,6-dihydro-2H-pyran 
• 856410-60-1 tert-Butyl-{(S)-1-[(R)-3-(4-methoxy-benzyloxy)-2-methyl-propyl]-but-3-enyloxy}-dimethyl-silane 
• 848691-92-9 (Z)-5-(tert-butyldimethylsilyl)oxy-3-methyl-3-penten-1-al 
• 848691-93-0 dimethyl 2-{(4R,5S)-2,2-dimethyl-5-[2-(4-methoxybenzyloxy)ethyl]-[1,3]dioxolan-4-yl}-2-oxo-ethyl-1-phosphonate 
• 847835-00-1 6-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-8-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dienoic acid methyl ester 
• 856410-50-9 (2E,5Z)-7-(tert-butyldiphenylsilyl)oxy-1-{(4R,5S)-2,2-dimethyl-5-[2-(4-methoxybenzyloxy)ethyl]-[1,3]-dioxolan-4-yl}-5-methyl-hepta-2,5-dien-1-one 
• 856410-37-2 (2E,5Z)-(1R)-7-(tert-butyldiphenylsilyl)oxy-1-{(4R,5S)-2,2-dimethyl-5-[2-(4-methoxybenzyloxy)ethyl]-[1,3]-dioxolan-4-yl}-5-methyl-hepta-2,5-dien-1-ol 
• 856410-51-0 Benzoic acid (2E,5Z)-(S)-7-(tert-butyl-diphenyl-silanyloxy)-1-{(4R,5S)-5-[2-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-methyl-hepta-2,5-dienyl ester 
• 90865-70-6 [3R]-4-Benzyloxy-3-methylbutanal 
• 5949-05-3 (S)-Citronellal 
• 676474-20-7 acetic acid 4-methyl-2-methylene-5-[6-(2-oxo-ethyl)-3,6-dihydro-2H-pyran-2-yl]-pentyl ester 
• 362471-95-2 acetic acid 5-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-4-methyl-2-methylene-pentyl ester 
• 362471-87-2 2-{(2S)-3-[(2R,6R)-6-(2-[(tert)-butyl{dimethyl}silyloxy]ethyl)-3,6-dihydro-2H-pyran-2-yl]-2-methylpropyl}prop-2-en-1-ol 

Relevant academic research and scientific papers

Total synthesis of (-)-Laulimalide

(-)-Laulimalide (1), a structurally novel macrolide isolated in trace amounts from marine sponges, promotes abnormal tubulin polymerization and apoptosis in vitro, with a similar mode of action to that of Taxol-, but with potentially less susceptibility to multidrug resistance. Herein, a flexible and convergent asymmetric synthesis of (-)-laulimalide is described. This synthesis featured a highly diastereoselective Sakurai reaction of 2 with 3 and a regioselective macrolactonization of an unprotected vicinal diol. Laulimalide was synthesized in 25 steps (longest linear; 36 overall) in 3.5% overall yield, providing a uniquely short and efficient route to 1 and its analogues. Copyright

Total synthesis of laulimalide: Assembly of the fragments and completion of the synthesis of the natural product and a potent analogue

Herein, we present a full account of our efforts to couple the northern and the southern building blocks, the synthesis of which were described in the preceding paper, along with the modifications required to ultimately lead to a successful synthesis of laulimalide. Key highlights include an exceptionally efficient and atom-economical intramolecular ruthenium-catalyzed alkene-alkyne coupling to build the macrocycle, followed by a highly stereoselective 1,3-allylic isomerization promoted by a rhenium complex. Interestingly, the designed synthetic route also allowed us to prepare an analogue of the natural product that possesses significant cytotoxic activity. We also report a second generation route that provides a more concise synthesis of the natural product. All in one piece: Efforts to couple the northern and southern building blocks, synthesized in the preceding paper, along with modifications required to lead to a successful synthesis of laulimalide are discussed. Interestingly, the designed synthetic route also allowed the preparation of an analogue of the natural product that possesses significant cytotoxic activity (see scheme). A more concise, second-generation route to the natural product is also described. Copyright

Evaluating transition-metal-catalyzed transformations for the synthesis of laulimalide

(Chemical Equation Presented) Laulimalide is a structurally unique 20-membered marine macrolide displaying microtubule stabilizing activity similar to that of paclitaxel and the epothilones. The use of atom-economical transformations such as a Rh-catalyze

Total synthesis of (-)-laulimalide: Pd-catalyzed stereospecific ring construction of the substituted 3,6-dihydro[2H]pyran units

(Chemical Equation Presented) The potent anticancer agent (-)-laulimalide (1) was prepared through a versatile method that should allow access to other marine natural products. Key steps included a Pd-catalyzed 1,3 chirality transfer of an allylic alcohol

LAULIMALIDE ANALOGS AND USES THEREOF

The present invention provides compounds having formula 1: (I) and pharmaceutically acceptable derivatives thereof, wherein R1-R10, q, t, X0, X1, A, B, D, E, G, J, K, L, M and Z are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders associated with cellular hyperproliferation.

Synthesis and biological evaluation of (-)-laulimalide analogues

Analogues of the marine natural product (-)-laulimalide were prepared by total synthesis and evaluated in vitro for anticancer activity.

Total synthesis of the microtubule stabilizing antitumor agent laulimalide and some nonnatural analogues: The power of sharpless' asymmetric epoxidation

Three different routes are described for the synthesis of deoxylaulimalide (3), which is the immediate precursor of the marine sponge metabolite laulimalide (1). These routes mainly differ with respect to their ring closing step. Thus, route 1 uses a Still-Gennari olefination, route 2 a Yamaguchi lactonization, and route 3 an intramolecular allylsilane-aldehyde addition for establishing the macrocyclic structure. The unprotected deoxy derivative 3 was subjected to Sharpless' asymmetric epoxidation (SAE). With (R,R)-tartrate the 16,17-epoxide laulimalide (1) is formed selectively, whereas (S,S)-tartrate generates the 21,22-epoxide 142. This demonstrates the high reagent control involved in the SAE process, which in this case is used to achieve high stereo- and regioselectivity. Laulimalide and some derivatives thereof have been tested with respect to antitumor activity and compared to standard compounds paclitaxel and epothilone B.

A de novo enantioselective total synthesis of (-)-laulimalide

An enantioselective total synthesis of the naturally occurring anticancer agent (-)-laulimalide is described. The synthesis is characterized by extensive use of new reaction methodologies based on catalytic asymmetric acyl halide-aldehyde cyclocondensatio

Asymmetric total synthesis of (-)-laulimalide: Exploiting the asymmetric glycolate alkylation reaction

A concise total synthesis of the potent antitumor macrolide (-)-laulimalide is described. The observation that homoallylic (or latent homoallylic) C-O bonds are present at C5, C9, C15, C19, and C23 led to the strategic decision to rely heavily on the asym

Total synthesis of microtubule-stabilizing agent (-)-laulimalide

An enantioselective first total synthesis of laulimalide (1) is described. Laulimalide, a remarkably potent antitumor macrolide, has been isolated from the Indonesian sponge Hyattella sp. and the Okinawan sponge Fasciospongia rimosa. Laulimalide represents a new class of antitumor agents with significant clinical potential. The synthesis is convergent and involved the assembly of C3-C16 segment 4 and C17-C28 segment 5 by Julia olefination. The sensitive C2-C3 cis-olefin functionality was installed by Yamaguchi macrolactonization of a hydroxy alkynic acid followed by hydrogenation of the resulting alkynoic lactone over Lindlar's catalyst. Initial attempts of intramolecular Still's variant of Horner - Emmons olefination between the C19-phosphonocetate and C3-aldehyde provided a 1:2 mixture of cis- and trans-macrolactones. The trans-isomer was photo-isomerized to a mixture of cis- and trans-isomers. The other key steps involved ring-closing olefin metathesis to construct both dihydropyran units, stereoselective anomeric alkylation to functionalize the dihydropyran ring, stereoselective reduction of the resulting alkynyl ketone to set the C20-hydroxyl stereochemistry, and a novel Julia olefination protocol for the installation of the C13-exomethylene unit. The sensitive epoxide at C16-C17 was introduced in a highly stereoselective manner by Sharpless epoxidation at the final stage of the synthesis.