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Synthesis 2010(21): 3657-3662
DOI: 10.1055/s-0030-1258244
DOI: 10.1055/s-0030-1258244
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkStereoselective Total Synthesis of (3R,5R)-5-Hydroxy-de-O-methyllasiodiplodin via the Prins Cyclization
Weitere Informationen
Received
5 July 2010
Publikationsdatum:
07. September 2010 (online)
Publikationsverlauf
Publikationsdatum:
07. September 2010 (online)
Abstract
A practical stereoselective total synthesis of (3R,5R)-5-hydroxy-de-O-methyllasiodiplodin has been accomplished via Prins cyclization. It exhibits potato microtuber inducing activity. The synthetic sequence involves Prins cyclization, reductive opening of the pyran ring, esterification, and ring-closing metathesis (RCM) as the key steps.
Key words
Prins cyclization - ring-closing metathesis - esterification - reductive ring opening - lactone
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