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Synthesis of the C38−C44 Segment of Altohyrtin A − With an Addendum on the Preparation of 8‐Oxabicyclo[3.2.1]oct‐6‐en‐3‐one
Author(s) -
Kim H.,
Hoffmann H. Martin R.
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200006)2000:12<2195::aid-ejoc2195>3.0.co;2-c
Subject(s) - stereocenter , chemistry , addendum , yield (engineering) , stereochemistry , furan , acetone , organic chemistry , enantioselective synthesis , catalysis , political science , law , metallurgy , materials science
The densely funkctionalized C38−C44 segment F of altohyrtin A with its five contiguous stereogenic centers was prepared in 10 steps and in 28 % overall yield (two steps per stereogenic center), from 8‐oxabicyclo[3.2.1]oct‐6‐en‐3‐one as a template. The preparation of the title compound 1 , m.p. 38 °C, is described on a 0.5‐ M scale in a three‐step‐two‐stage reaction from acetone and furan. The oxacycle was stored without change at room temperature.