72629-68-6

Usage

InChI:InChI=1/C20H32O2/c1-14(2)18-13-12-16(4)9-6-8-15(3)10-7-11-17(5)19(21)20(18)22/h8,11-14,19-22H,6-7,9-10H2,1-5H3/b15-8-,16-12-,17-11-,18-13-/t19-,20-/m1/s1

Upstream product

• 93787-91-8 E,E,E-12-hydroxyfarnesyl acetate 
• 4128-17-0 (2E,6E)-farnesyl acetate 
• 123979-87-3 Ethyl (2Z,4E,8E,12E)-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate 
• 123979-88-4 Ethyl (2Z,4E,8E,12E)-14-hydroxy-2-(1-methylethyl)-5,9,13-trimethyl-2,4,8,12-tetradecatetraenoate 
• 123979-90-8 (2Z,4E,8E,12E)-2-Isopropyl-5,9,13-trimethyl-tetradeca-2,4,8,12-tetraene-1,14-diol 
• 148515-21-3 ethyl 2-(diethoxyphosphoryl)-3-methylbutyrate 
• 502-67-0 Farnesal 
• 123979-89-5 (2Z,4E,8E,12E)-2-Isopropyl-5,9,13-trimethyl-tetradeca-2,4,8,12-tetraenedial 
• 77965-78-7 Flaccidoxide 
• 77965-80-1 11,12-Epoxy-13,14-dihydroxycembrene-C 
• 40266-21-5 (2E,6E,10E)-3,7,11-trimethyl-12-oxododeca-2,6,10-trien-1-yl acetate 

Downstream Products

• 123853-59-8 C₃₈H₅₀N₂O₄ 
• 123853-59-8 C₃₈H₅₀N₂O₄ 
• 123853-59-8 C₃₈H₅₀N₂O₄ 

Relevant academic research and scientific papers

Further Cembranoid Derivatives from the Red Sea Soft Corals Alcyonium flaccidum and Lobophytum crassum

The cembranoid content of two soft corals has been investigated.Three compounds were isolated from Alcyonium flaccidum and were found to be cembrene-C (1), sarcophytol-B (2), and the as yet unreported 11,12-epoksy-13-hydroxy-14-acetoxycembrene-C (3), which was named flaccidoxide. From Lobophytum crassum, another soft coral whose chemical content was found to change remarkably with place of collection, were isolated two new 13-hydroxylobolides (7 and 8) in addition to lobolide (6), and their structures were characterized.The 13C NMR spectra of all the above compounds were assigned.

Concise and efficient total syntheses of (±)-sarcophytols A and B, two antitumor cembrane diterpenoids, by an intramolecular Mcmurry olefination strategy

Efficient total syntheses of (±)-sarcophytol A and B, two antitumor cembrane diterpenoids isolated from marine soft corals, were presented by a low-valent titanium-mediated intramolecular McMurry olefination strategy starting from trans, trans-farnesol.

ATTEMPTED ACID-CATALYZED TRANSANNULAR REACTIONS IN THE CEMBRANOIDS

Several cembrane diterpenes were treated by various acids under different experimental conditions.All tested compounds were found to be acid sensitive, leading either to local chemical transformations (e.g. opening of epoxides), to transannular reactions and/or to unidentified mixtures.Sarcophine (7), the principal cembrane tested, was found to afford either all types of possible epoxide opening products (11-22), or, by a transannular reaction, when treated with SnCl4, two tetrahydrooxepine derivatives (23 and 24).The structure determination of the various derivatives of sarcophine was based mainly on the 1H and 13C-NMR spectra and also on several chemical transformations.Flaccidoxide (8), another cembranoid examined, was found to yield, with Zn/Cu couple, the expected deoxygenation product (sarcophytol-B, 32) together with an unexpected transannular reaction product (33).The structure, including the stereochemistry, of the latter THF-derivative of 8 (33) was elucidated by NMR and chemical reactions.