105880-10-2

Upstream product

• 119840-65-2 (2R,4aR,6R,8aS)-Octahydro-2-<(1S,4R)-1,4-dihydroxy-4-<(2S,5R)-tetrahydro-5-(1-hydroxy-1-methylethyl)-2-methylfuran-2-yl>-1-methylbutyl>-6-<(S)-1-hydroxy-1,5-dimethylhex-4-enyl>-8a-methylpyrano<3,2-b>pyran 
• 121693-71-8 ((1S,2R,7R)-1,6,6-Trimethyl-3,5,10-trioxa-bicyclo[5.2.1]dec-2-yl)-methanol 
• 121693-73-0 2-((1S,2R,7R)-1,6,6-Trimethyl-3,5,10-trioxa-bicyclo[5.2.1]dec-2-yl)-ethanol 
• 121693-64-9 (1S,2R,7R)-2-(2-Bromo-ethyl)-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]decane 
• 304465-96-1 Acetic acid (1S,2R)-1-benzyloxymethyl-2-hydroxy-2,6-dimethyl-hept-5-enyl ester 
• 240133-61-3 (E)-(R)-7-Benzyloxy-6-hydroxy-2-methyl-hept-2-enoic acid ethyl ester 
• 304465-95-0 (2S,3R)-1-(benzyloxy)-3,7-dimethyloct-6-ene-2,3-diol 
• 306775-68-8 (2S,3S)-1-O-benzyl-2,3-epoxygeraniol 
• 304466-04-4 (R)-1-((2S,5R)-5-Bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-ethane-1,2-diol 
• 240133-55-5 5-bromo-2,6,6-trimethyl-(5R)-tetrahydropyran-2-carbaldehyde 
• 93381-43-2 (R)-(-)-1-benzyloxy-2,5-pentanediol 
• 121693-59-2 (2R,4aR,6R,8aS)-6-((2S,5R)-5-Bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-carbaldehyde 
• 77697-15-5 (R)-(-)-γ-benzyloxymethyl-γ-butyrolactone 
• 126-90-9 (S)-(+)-linalool 

Downstream Products

• 66873-47-0 thyrsiferol monoacetate 
• 66873-47-0 thyrsiferyl 18-acetate 
• 66873-47-0 Acetic acid (1R,4S)-4-[(4aS,6S,8aR)-6-((2R,5S)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-8a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl]-4-hydroxy-1-[(2R,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-pentyl ester 

Relevant academic research and scientific papers

Teurilene and thyrsiferyl 23-acetate, meso and remarkably cytotoxic compounds from the marine red alga Laurencia obtusa (Hudson) Lamouroux

Two new cyclic ethers consisting of a squalene carbon skeleton have been isolated from the red alga L. obtusa. The absolute stereostructure of teurilene was elucidated by the X-ray crystallographic method, and the structure of thyrsiferyl 23-acetate was established from spectral and chemical evidence.

Cytotoxic Squalene-Derived Polyethers from the Marine Red Alga Laurentia obtusa (Hudson) Lamouroux

Five new cytotoxic triterpenoids with squalene carbon skeleton have been isolated from the title alga.The structures of 15(18)-anhydrothyrsiferyl diacetate, 15-anhydrothyrsiferyl diacetate, and magireol-A were confirmed by the spectral and chemical methods.The structures of magireol-B and -C were deduced from spectral data.

Total synthesis of thyrsiferyl 23-acetate, a specific inhibitor of protein phosphatase 2A and an anti-leukemic inducer of apoptosis

A convergent synthetic entry to the squalenoid polyether system has been developed and applied to the biologically active marine natural products thyrsiferyl 23-acetate (1a), thyrsiferol (1b), thyrsiferyl 18-acetate (1c), and thyrsiferyl 18,23-diacetate (

Total Syntheses of (+)-Thyrsiferol, (+)-Thyrsiferyl 23-Acetate, and (+)-Venustatriol

The first total syntheses of (+)-thyrsiferol (1), (+)-thyrsiferyl 23-acetate (3), and (+)-venustatriol (5) have been accomplished in a stereoselective manner.An effective synthetic scheme to construct the BC ring system, which adopts a chair/twist-boat conformation, was first developed by means of a model study.This method involves stereoselective formation of the strained C ring by intramolecular attack of the C7-hydroxyl group at the C3-postion of the 2,3-epoxy alcohol, employing titanium tetraisopropoxide as an acidic activator.Based on the information accumulated in the model study and retrosynthetic considerations, the total syntheses of 1,3, and 5 were performed in the sequence of (1) construction of the BC ring system equipped with a C1-C6 carbon unit, (2) elongation of the C17-C24 carbon chain, (3) formation of a D ring through the stereoselective epoxidation of the 4-en-1-ol system and successive cyclization, and (4) construction of the A ring by bromonium ion induced cyclization of the 4-en-1-ol system.

TOTAL SYNTHESIS OF VENUSTATRIOL

Venustatriol (1) has been synthesized by an enantioselective and convergent route via key intermediates 9 and 15.

TERPENOIDS OF THE RED ALGA LAURENCIA PINNATIFIDA

The structures of three brominated terpenoids which are natural products from the red alga Laurencia pinnatifida (Gmal.Lamour) are described.The structures of the sesquiterpenes 4 and 5 were determined by spectral comparison and chemical interconversion.The structure of the squalene-derived terpenoid 8 was secured by chemical transformation into thyrsiferol, a brominated triterpene previously isolated from the red alga Laurencia thyrsifera.