An Approach to the Total Synthesis of Aphidicolin
Year: 2025
Type: dissertation
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).
Source: Caltech Library
DOI: 10.7907/rerp-ya50
Author: Aristoff, Paul Adrian
Institution: California Institute of Technology
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7101445170
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