Journal
TETRAHEDRON LETTERS
Volume 44, Issue 3, Pages 543-547Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(02)02618-7
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The stereospecific total synthesis of (+)-N-a-methyl-16-epipericyclivine (1) was completed [from D-(+)-tryptophan methyl ester] in an overall yield of 42% (eight reaction vessels). The optical rotation {[alpha](D) +22.8 (c 0.50, CHCl3)} obtained on this material confirmed that the reported optical rotation {[alpha](D) 0 (c 0.50, CHCl3)} was biogenetically unreasonable. The first total synthesis of (-)-alkaloid Q(3) (5) and (-)-panarine (6), via the intermediate vellosimine (18), is also described. (C) 2002 Elsevier Science Ltd. All rights reserved.
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