Synthesis of 11,12-Epoxydrim-8,12-en-11-ol, 11,12-Diacetoxydrimane, and Warburganal from (−)-Sclareol

Abstract

The first syntheses are reported for recently isolated drimanes 11,12-epoxydrim-8,12-en-11-ol (2) and 11,12-diacetoxydrimane (3), from (-)-sclareol (1). Furthermore, two efficient new routes to the potent bioactive warburganal (4) starting also from 1 are described.

Total Syntheses of Sesterterpenoid Ansellones A and B, and Phorbadione

“…[19] Oxidation of (+ +)-20 with SeO 2 ,followed by hydrolysis and IBX oxidation provided the dienone aldehyde (À)-21.T he zinc-mediated Barbier-type reaction of (À)-21 and (À)-10 afforded am ixture of two separable diastereomers, (+ +)-22 a and (À)-22 b (22 a/22 b = 1.7:1) in 74 %c ombined yield. Therefore,w ep repared the sesquiterpene (+ +)-20 with 57 %overall yield in eight steps from (+ +)-sclareolide (11)byfollowing the established procedures.…”

Synthetic and Biological Studies of Sesquiterpene Polygodial: Activity of 9‐Epipolygodial against Drug‐Resistant Cancer Cells

“…However,t he results of mechanistic studies have complicated matters by questioning whether the anticancere ffects of vanilloids are mediated by TRPV1,a nd have revealed that TRPV1 antagonists generally do not prevent vanilloid agonist-induced cell death. [27,[29][30][31][32] Despite severalr eports of cytotoxic activity associated with polygodial, [33][34][35][36][37][38][39] to our knowledge,t his TRPV1 agonist or related bicyclic sesquiterpene dialdehydesh ave not been investigated as potential anticancer agents. This report detailso ur synthetic study of polygodial (1), the generation of as eries of polygodiala nalogues, and the evaluation of the synthesized compounds for TRPV1 and anticancer activities.…”

Elimination of C-8-functional groups from driman-8α,11-diol-11-monoacetate and-diacetate

“…, % Ratio of acetates (4)(5)(6), % Yield of hydrocarbon (12), % Driman-8α,11-diol-11monoacetate (7) 7 7 7 7 7…”

“…), CH 3 CN, 18-20°C (c) CF 3 SO 3 SiMe 3 (1 eq. ), CH 3 Obviously it would be interesting to perform regioselective elimination of a C 8 -functional group of 7 or 8 to form only one of the possible acetates (4)(5)(6). The use of several reagents to achieve this goal has been reported.…”

“…Poigny et al [11] dehydrated 7 with an excess of SOCl 2 in pyridine in the presence of 4-dimethylaminopyridine (DMAP) and produced a mixture of acetates (4)(5)(6) in which albicanylacetate (5) predominated. Oxidation of this mixture by m-chloroperbenzoic acid gave the epoxides of 4 and 6 whereas albicanylacetate (5) was unchanged and isolated chromatographically in 61% yield.…”