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. 2011 Mar 4;13(5):1234-7.
doi: 10.1021/ol200119h. Epub 2011 Jan 27.

Synthesis of (±)-7-hydroxylycopodine

Hong-Yu Lin  1 , Barry B Snider
Affiliations

Synthesis of (±)-7-hydroxylycopodine

Hong-Yu Lin et al. Org Lett. .

Abstract

A six step synthesis of (±)-7-hydroxylycopodine has been achieved in 5% overall yield. In the key step, a Prins cyclization of a bicyclic keto alkyne in 60% H(2)SO(4) forms a tricyclic dihydroxy amino ketone.

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Figures

Scheme 1
Scheme 1. Retrosynthesis of 7-Hydroxylycopodine
Scheme 2
Scheme 2. Unsuccessful Approach to Diketone
Scheme 3
Scheme 3. Synthesis of Model Tricyclic Hydroxy Ketone 24
Scheme 4
Scheme 4. Synthesis of 7-Hydroxylycopodine (4)
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