Total Synthesis of Amphilectane-Type
Diterpenoid (±)-7-Isocyanoamphilecta-11(20),15-diene

Hiroaki Miyaoka; Yusuke Okubo

doi:10.1055/s-0030-1259514

LETTER

Total Synthesis of Amphilectane-Type Diterpenoid (±)-7-Isocyanoamphilecta-11(20),15-diene

Hiroaki Miyaoka*, Yusuke Okubo
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan
Fax: +81(42)6763073; e-Mail: miyaokah@toyaku.ac.jp;

Abstract

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Abstract

The total synthesis of amphilectane-type diterpenoid ()-7-isocyanoamphilecta-11(20),15-diene, isolated from the tropical marine sponge Cymbastela hooperi, was achieved. The synthesis involves construction of a cis-decalin ring by an intramolecular Diels-Alder reaction and construction of an all-trans-perhydrophenalene ring by an intramolecular Michael reaction as the key steps.

Key words

total synthesis - 7-isocyanoamphilecta-11(20),15-diene - isocyanide - intramolecular Diels-Alder reaction - intramolecular Michael reaction

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References

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