Drimenol: A versatile synthon for compounds with trans-drimane skeleton
Manuel Cortés1, Virginia Delgado, Claudio Saitz
1Departamento de Química Orgánica. Facultad de Química, Pontificia Universidad Católica de Chile, Vicuña Mackenna 4860, 7820436, Santiago, Chile.
Natural Product Communications
|May 13, 2011
Summary
This review details drimenol synthesis and its use as a chiral building block for drimane-type sesquiterpenes. It covers isolation, configuration, and various synthetic strategies, including biomimetic approaches.
Area of Science:
- Natural Product Chemistry
- Organic Synthesis
- Medicinal Chemistry
Background:
- Drimenol and related drimane-type sesquiterpenes are important natural products.
- Previous reviews have covered sesquiterpenes broadly, but not exclusively drimenol.
- Drimenol serves as a key synthon in synthesizing complex molecules.
Purpose of the Study:
- To provide the first comprehensive review focused solely on drimenol.
- To summarize synthetic routes for racemic and enantiopure drimenol.
- To highlight drimenol's role as a versatile synthon for drimane derivatives.
Main Methods:
- Review of published literature on drimenol synthesis and isolation.
- Analysis of synthetic strategies, including total synthesis and use of natural (-)-drimenol.
- Examination of biomimetic cyclization and microbiological functionalization methods.
Main Results:
- Compilation of synthetic routes to racemic and (-)-drimenol, including historical isolation and configuration determination.
- Overview of synthetic pathways utilizing (-)-drimenol as a chiral synthon.
- Discussion of total syntheses and biomimetic approaches starting from trans-farnesol.
Conclusions:
- Drimenol is a pivotal compound in the synthesis of drimane-type sesquiterpenes.
- Diverse synthetic methodologies exist for accessing drimenol and its derivatives.
- This review consolidates knowledge on drimenol, facilitating future research in natural product synthesis.
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