194342-84-2

Upstream product

• 1826-67-1 vinyl magnesium bromide 
• 80910-01-6 (S)-2-[(4-methoxybenzyloxy)methyl]oxirane 
• 3536-96-7 vinylmagnesium chloride 
• 80910-01-6 (R)-2-(((4-methoxybenzyl)oxy)methyl)oxirane 
• 824-94-2 p-methoxybenzyl chloride 
• 121289-23-4 p-methoxybenzyloxyacetaldehyde 
• 124821-92-7 d-B-allylbis(2-isocaranyl)borane 
• 24850-33-7 allyltributylstanane 

Downstream Products

• 194342-85-3 2-[(R)-1-(4-Methoxy-benzyloxymethyl)-but-3-enyloxy]-tetrahydro-pyran 
• 1164115-06-3 (R)-5-(4-methoxybenzyloxy)-4-(triisopropylsilyloxy)pent-1-ene 
• 862475-35-2 (R)-5-(p-methoxybenzyloxy)-4-(triethylsiloxy)-1-pentene 
• 909570-87-2 (R)-6-((4-methoxybenzyloxy)methyl)-5,6-dihydropyran-2-one 
• 1012367-41-7 tert-butyl-(R)-(1-(4-methoxybenzyloxy)pent-4-en-2-yloxy)dimethylsilane 
• 174623-89-3 ((1S,2R)-1-Benzyl-2-methoxymethoxy-pent-4-enyl)-methyl-carbamic acid benzyl ester 
• 127041-77-4 ((1S,2R)-1-Benzyl-2-hydroxy-pent-4-enyl)-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Total Synthesis of Kalimantacin A

The kalimantacins make up a family of hybrid polyketide-nonribosomal peptide-derived natural products that display potent and selective antibiotic activity against multidrug resistant strains of Staphylococcus aureus. Herein, we report the first total synthesis of kalimantacin A, in which three fragments are prepared and then united via Sonogashira and amide couplings. The enantioselective synthetic approach is convergent, unlocking routes to further kalimantacins and analogues for structure-activity relationship studies and clinical evaluation.

Total Synthesis of the Anticancer Marine Natural Product Mycalol

This communication describes a synthetic study of the originally proposed structure of mycalol (1) and the total synthesis of the actual structure of the anticancer marine natural product mycalol (2). The total synthesis of the originally proposed structu

A highly stereoselective formal synthesis of hapalosin

A flexible and highly diastereoselective formal synthesis of hapalosin, a cyclodepsipeptide isolated from the blue green alga Hapalosiphon welwitschii and having multidrug-resistance-reversing activity is described. The synthetic route involves the addition of organometallic reagent to N-tert- butanesulfinylimine, Jung nonaldol aldol reaction, and Yamaguchi esterification as key steps. Georg Thieme Verlag Stuttgart · New York.

Good timing in total synthesis: The case of phoslactomycin A

The importance for the right order of functional group introduction and manipulation (good timing) was demonstrated in the course of a total synthesis of phoslactomycin A. The synthetic strategy comprised a CuIthiophene carboxylate (CuTC, Liebeskind's reagent)-mediated coupling to introduce the Z, Z-diene at the final stage of the synthesis in the presence of a protected phosphate. Key features for the assembly of the C1-C13 fragment were an asymmetric dihydroxylation, an Evans-aldol reaction and an advanced protective group strategy. The C14-C21 fragment was accessible via an asymmetric 1, 2-addition to cyclohexenone and a subsequent diastereoselective ketone reduction. One crucial task was the dihydroxylation of the C8-C9 alkene, the introduction of the C6-C7 double bond and the generation of the C25-nitrogen functionality. A second example consisted of the best sequence for the generation of the functional groups in the core part (first phosphorylation, second iodo-olefination, third azide/carbamate conversion). The synthetic solutions from this approach are compared with the already existing contributions in the phoslactomycin area.

Total synthesis of phoslactomycin A

A convergent total synthesis of the PP2A-inhibitor phoslactomycin A was achieved using a CuTC-mediated coupling of an alkenyl iodide C1-C13 fragment with an C14-C21 alkenyl stannane in the presence of a protected phosphate. Key features for the assembly of the C1-C13 fragment were an asymmetric dihydroxylation, an Evans-Aldol reaction, and a well-balanced protective group strategy. An asymmetric 1,4addition to cyclohexenone was the key step in the preparation of the C14-C21 fragment.

Enantioselective synthesis of structurally intricate and complementary polyoxygenated building blocks of spongistatin 1 (altohyrtin a)

Enantioselective approaches to the construction of four complex building blocks of the structurally intricate marine macrolide known as spongistatin 1 are presented. The first phase of the synthetic effort relies on a practical approach to a desymmetrized, enantiomerically pure spiroketal ring system incorporating rings A and B. Concurrently, the C17-C28 subunit, which houses one-fifth of the stereogenic centers of the target in the form of rings C and D, was assembled via a composite of stereocontrolled aldol condensations. Once arrival at the entire C1-C28 sector had been realized, routes were devised to provide two additional highly functionalized sectors consisting of C29-C44 and C38-C51. A series of subsequent transformations including cyclization of the E ring and hydroboration to afford the B-alkyl intermediate for the key Suzuki coupling to append the side chain took advantage of efficient stereocontrol. Ultimately, complete assembly and functionalization of the western EF sector of spongistatin was thwarted by an inoperative Suzuki coupling step intended to join the side chain to the C29-C44 sector, and later because of complications due to protecting groups, which precluded the complete elaboration of the late stage C29-C51 intermediate.

Total synthesis of (R)-(+)-goniothalamin and (R)-(+)-goniothalamin oxide: first application of the sulfoxide-modified Julia olefination in total synthesis

A short and efficient synthesis of (R)-(+)-goniothalamin 1 and (R)-(+)-goniothalamin oxide 2 is described. During this approach, the sulfoxide-modified Julia olefination was used as a key step to connect aldehyde 5 to sulfoxide 6. The desired styryl-containing adduct is obtained in good yield and with excellent E/Z selectivity.

The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: The CD-spiroacetal segment

Stereocontrolled syntheses of the C16-C28 CD-spiroacetal subunit of altohyrtin A/spongistatin 1 (1), relying on kinetic and thermodynamic control of the spiroacetal formation, are described. The kinetic control approach resulted in a slight preference (60: 40) for the desired spiroacetal isomer. The thermodynamic approach allowed ready access to the desired spiroacetal 2 by acid-promoted equilibration, Chromatographic separation of the C23 epimers and resubjection of the undesired isomer to the equilibration conditions. This scalable synthetic sequence provided multi-gram quantities of 2, thus enabling the successful completion of the total synthesis of altohyrtin A/spongistatin 1, as reported in Part 4 of this series. The Royal Society of Chemistry 2005.

(R)-Goniothalamin: Total syntheses and cytotoxic activity against cancer cell lines

The total syntheses of (R)-goniothalamin (1), a styryl lactone isolated from several Goniothalamus species, via catalytic asymmetric allylation of α-benzyloxyacetaldehyde (2), followed by ring-closing metathesis and Wittig olefination and via catalytic asymmetric allylation of trans-cinnamaldehyde (12), followed by ring-closing metathesis are reported. The antiproliferative activities of (R)-1 and its Z-isomer 10 as well as of the synthetic dihydropyranone intermediates 7 and 8 against eight different cancer cell lines are also described.

Stereochemistry of hydrogen removal from the 'unactivated' C-3 position of 4-hydroxybutyryl-CoA catalysed by 4-hydroxybutyryl-CoA dehydratase.

(R)- and (S)-gamma-[3-(2)H(1)]butyrolactones have been synthesised from (R)- and (S)-glycidol, respectively, and used to demonstrate that it is the pro-(S) hydrogen atom that is stereospecifically abstracted from C-3 of 4-hydroxybutyryl-CoA by 4-hydroxybu