Synlett 2011(4): 547-550  
DOI: 10.1055/s-0030-1259514
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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;
Further Information

Publication History

Received 8 December 2010
Publication Date:
27 January 2011 (online)

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.