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Mannich-type reaction of methyl phenylacetate with the N-tert-butylsulfinyl imine derived from (R)-tert-butylsulfinamide and (Z)-14-(pyridin-3'-yl)tetradec-11-enal has been used as the key step in the first asymmetric synthesis of (-)-nakinadine A. Both the 2,3-syn- and 2,3-anti-diastereoisomers were prepared; comparison of spectroscopic and specific rotation data facilitated assignment of the absolute (2S,3R,Z)-configuration within the natural product. (-)-(2S,3R,Z)-Nakinadine A was prepared in 10 steps from 11-bromoundecan-1-ol, in 10% overall yield, 97:3 dr [(Z):(E) ratio], and >98% ee.

Original publication

DOI

10.1021/ol500096r

Type

Journal article

Journal

Org Lett

Publication Date

07/03/2014

Volume

16

Pages

1354 - 1357

Keywords

Alkaloids, Animals, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Porifera, Pyridines, Stereoisomerism