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Synthesis 2010(9): 1473-1478
DOI: 10.1055/s-0029-1218679
DOI: 10.1055/s-0029-1218679
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereoselective Total Synthesis of (-)-Colletol by Prins Cyclisation
Weitere Informationen
Received
23 November 2009
Publikationsdatum:
19. Februar 2010 (online)
Publikationsverlauf
Publikationsdatum:
19. Februar 2010 (online)
Abstract
A simple and efficient asymmetric total synthesis of the bis-macrolactone (-)-colletol was accomplished, proving the versatility of the Prins cyclisation in natural product synthesis. The synthesis mainly relies upon reductive opening of a pyran ring, Mitsunobu inversion, the Wittig reaction, and Yamaguchi macrolactonisation as the key steps.
Key words
natural products - Prins cyclization - Mitsunobu reaction - macrolactonization - lactones
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References
(R)-Pent-4-en-2-ol(9) is commercially available, e.g. from Aldrich.