Synthesis of FF8181-A

Total Synthesis of Cinnamodial-Based Dimer (−)-Capsicodendrin

“…Secondary alcohol moiety in 14 was subsequently oxidized with Dess–Martin periodinane to produce ketone 15 in 99% yield. For the introduction of the tertiary allylic alcohol moiety that is present in cinnamodial ( 1 ), we envisioned to apply the epoxydation/β-elimination sequence that was also utilized in Watanabe’s synthesis of FF8181-A . In the event, oxidation of tetrasubstituted olefin 15 with m CPBA resulted in epoxide 8 as a single diastereomer in 93% yield.…”

“…For the introduction of the tertiary allylic alcohol moiety that is present in cinnamodial (1), we envisioned to apply the epoxydation/β-elimination sequence that was also utilized in Watanabe's synthesis of FF8181-A. 22 In the event, oxidation of tetrasubstituted olefin 15 with mCPBA resulted in epoxide 8 as a single diastereomer in 93% yield. Treatment of ketone 8 with DBU induced a βelimination to yield allylic alcohol 16 in quantitative yield.…”

Synthesis of (−)-Chamobtusin A from (+)-Dehydroabietylamine

“…On the basis of this hypothesis, the biomimetic aza-cyclization was employed as a key reaction in our synthesis of (±)- 1 , as outlined in Scheme . Our racemic synthesis commenced with the transformation of the known alchohol 2 into 3 through a four-step sequence. Compound 4 , a precursor for intramolecular aza-cyclization, could be obtained from 3 through epoxidation of the double bond followed by side-chain elongations at C11 and C13 (chamobtusin A numbering).…”

Natural sesquiterpenoids

“…62 Both enantiomers of the sesquiterpene FF8181-A have been synthesized permitting the determination of the absolute configuration of the natural compound as 70. 63 The bicyclic sesquiterpene nanaimonal has been synthesized in a biomimetic manner. 64 An asymmetric synthesis of (+)-6 0hydroxyarenarol, a possible biosynthetic precursor of popolohuanone E, has been accomplished.…”