Expedient Access to Enantiopure Cyclopentanic Natural Products: Total Synthesis of (-)-Cyclonerodiol

Following the principles of collective total synthesis, a number of natural products sharing an optically pure, multifunctional, cyclopentanic core were synthesized from a common precursor: plinol A (1). This intermediate was efficiently obtained in only four steps from (-)-linalool (2) using as the...

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Bibliographic Details
Published in:Natural product communications 2015-01, Vol.10 (1), p.1-4
Main Authors: Morales, Carmen Pérez, Herrador, M. Mar, del Moral, José F. Quílez, Barrero, Alejandro F.
Format: Article
Language:English
Subjects:
Cyclopentanes - chemical synthesis
Feasibility Studies
Monoterpenes - chemistry
Sesquiterpenes - chemical synthesis
Terpenes - chemical synthesis
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Summary:Following the principles of collective total synthesis, a number of natural products sharing an optically pure, multifunctional, cyclopentanic core were synthesized from a common precursor: plinol A (1). This intermediate was efficiently obtained in only four steps from (-)-linalool (2) using as the key step a Ti(III)-mediated diastereoselective radical cyclization. The feasibility of this approach was confirmed with the expedient enantiospecific synthesis of cyclonerodiol (3), and the formal synthesis of chocol G (4) and piperitone (5).
ISSN:1934-578X
1555-9475
DOI:10.1177/1934578X1501000103