Enantiospecific formal total synthesis of (+)-fawcettimine.

Total synthesis of (+)-fawcettimine.

The fawcettimine class of Lycopodium alkaloids consists of over 60 natural products. Typically, these tetracyclic compounds contain a single quaternary carbon center and are derived biosynthetically from the lycopodane core through an oxidative rearrangement reaction. In 1959, the first member of this class, fawcettimine (1), was isolated by Burnell in the Blue Mountain Range of Jamaica. Inubus...

Natural Product Synthesis

The Lycopodium alkaloids are a family of structurally complex natural products, which have provoked long-term interests in their total syntheses because of their unique and fascinating architectures and potential biological activities. In particular, fawcettimine-type Lycopodium alkaloids, such as fawcettimine (1) and fawcettidine (2) (Scheme 1), have attracted broad attention from the syntheti...

Concise Enantiospecific Total Synthesis of Tubingensin A

We report the enantiospecific total synthesis of (+)-tubingensin A. Our synthesis features an aryne cyclization to efficiently introduce the vicinal quaternary stereocenters of the natural product and proceeds in only nine steps (longest linear sequence) from known compounds.

Enantiospecific first total synthesis of cucumin-H

Enantiospecific total syntheses of(–)-valeranone

Two convenient methodologies have beendescribed for the enantiospecific synthesis of (–)-valeranone 1. The hydrindanone 12, obtained from the readily andabundantly available monoterpene (R)-carvone,has been converted into the ketoaldehyde 16via the alkene 15b. In anotherdirection the lactone 18, obtainedfrom the hydrindanone 12, has beenelaborated into the ketoaldehyde 16employing two methodolo...