115268-43-4

Basic information

• Product Name: (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
• Synonyms: (-)-Laulimalide; Fijianolide B; Laulimalide
• CAS NO: 115268-43-4
• Molecular Formula: C₃₀H₄₂O₇
• Molecular Weight: 514.66504
• Mol File: 115268-43-4.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (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(CAS DataBase Reference)
• NIST Chemistry Reference: (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(115268-43-4)
• EPA Substance Registry System: (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(115268-43-4)

Safety Data

• Hazardous Substances Data: 115268-43-4(Hazardous Substances Data)

Usage

General Description

The chemical compound "(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" is a complex organic molecule with a long, multi-ring structure. It contains a hydroxy functional group at position 7 and a methylene group at position 5, along with other substituents. The compound is a tricyclic molecule with an oxygen bridge, and it features a double bond and a number of chiral centers. (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 may have potential biological or pharmaceutical relevance, but its specific properties and uses would need to be further investigated through research and experimentation.

Upstream product

• 445306-72-9 (2R,6S)-2-{(2R)-6-[3-(4-methoxybenzyloxy)-2-methylpropyl]-5,6-dihydro-2H-pyran-2-yl}-ethanol 
• 464914-19-0 (2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dien-1-ol 
• 273733-96-3 (5S)-5-(p-methoxy-benzyl)-methyl-3-phenyl-sulphonyl-dihydrofuran-2-one 
• 289473-02-5 (1E,3S,4S)-6-benzenesulfonyl-4-(4-methoxy-benzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-1-en-3-ol 
• 289473-00-3 (S)-6-Benzenesulfonyl-4-(4-methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-1-yn-3-ol 
• 289473-01-4 (4S)-6-benzenesulfonyl-4-(4-methoxy-benzyloxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-1-yn-3-one 
• 289473-04-7 (3S,4S)-6-Benzenesulfonyl-4-(4-methoxy-benzyloxy)-1-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-hex-1-yn-3-ol 
• 312695-89-9 2-[(2R,6S)-6-((R)-3-Benzyloxy-2-methyl-propyl)-5,6-dihydro-2H-pyran-2-yl]-ethanol 
• 312695-90-2 (2R)-3-{(2S,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methylpropan-1-ol 
• 312695-78-6 (2R,6S)-tert-butyl-(2-{6-[(2R)-3-iodo-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-dimethyl-silane 
• 312695-77-5 (2R,6S)-(2-{6-[(2R)-3-benzyloxy-2-methyl-propyl]-5,6-dihydro-2H-pyran-2-yl}-ethoxy)-tert-butyl-dimethyl-silane 
• 312695-82-2 (2S)-2-{(E)-2-[(4S,5S)-5-(2-benzenesulfonyl-ethyl)-2-(4-methoxy-phenyl)-[1,3]dioxolan-4-yl]-vinyl}-4-methyl-3,6-dihydro-2H-pyran 
• 312695-75-3 [(2R,6R),(2S),2S]-4-(3-{6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3,6-dihydro-2H-pyran-2-yl}-2-methylpropyl)-2-methoxymethoxypent-4-enal 
• 312695-76-4 (3S,4S,5E)-1-benzenesulfonyl-4-(4-methoxy-benzyloxy)-6-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]-hex-5-en-3-ol 

Relevant articles and documents

Macrocyclization via allyl transfer: Total synthesis of laulimalide [14]

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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

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

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.