Antimicrobial drimane-type

The total synthesis of the antimicrobial drimane-type sesquiterpene (-)-pereniporin A was achieved by the research team of K. Mori. The advanced intermediate bicyclic primary alcohol was first oxidized to the corresponding aldehyde using the Moffatt oxidation. Interestingly, the sensitive a-hydroxy aldehyde moiety in the product remained unchanged. The final step was a global deprotection followed by a spontaneous lactol formation. 

In 1994, six novel drimane-type sesquiterpenoids, mniopetals A-F (1-6) (Fig. (1)), were isolated by Anke and Steglich from the fermentation broth of Canadian Mniopetalum sp. 87256 [1, 2]. These natural products are known to inhibit the enzymatic activity of RNA-directed DNA-polymerases (reverse transcriptases) of the human immunodeficiency virus (HIV)-l, avian myeloblastosis virus (AMV), and moloney murine leukemia virus (MMuLV) as shown in Table 1. In addition, mniopetals exhibit moderate antimicrobial and cytotoxic activities. In the following year, a structurally and biologically similar natural product kuehnero-... 

A variety of drimane-type sesquiterpenes occur in the plant Polygonum hydropiper which is also known as water pepper [88-90]. The main constituents of the leaves and seed are (-)-polygodial (22) and (-)-tadeonal drime-7-en-l 1,12-dial. These compounds were found to be cytotoxic and inhibit plant growth [91]. The synthesis of polygodial (22), an antifeedant and antimicrobial agent [92], can be formed in a few steps from (2E, 6E)-famesyl pyrophosphate, 53 [93]. The intermediate of the reaction is drimenol (54) (Scheme 1). 

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