An Approach to the Total Synthesis of Aphidicolin

Author: Aristoff, Paul Adrian

Year: 1977

Degree: Dissertation (Ph.D.)

Advisor: Ireland, Robert E.

Committee Member: Unknown, Unknown

Option: Chemistry

DOI: 10.7907/rerp-ya50

Abstract

An approach to the total synthesis of the tetracyclic diterpene antibiotic aphidicolin i is described. The key intermediate ii was prepared in 19 steps (3% overall yield) from 2-methoxybenzosuberone. The key step involved the solvolysis of a spire system (generated from a Claisen rearrangement) with participation of a remote double bond. The desired trans A/B ring fusion was introduced in the model system iii (18,19-dinoraphidicolan-3-one), available from alcohol ii in 7 steps (40% overall yield).

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