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Scientific article
English

Enantioselective total synthesis of (−)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step

Published inTetrahedron, vol. 53, no. 27, p. 9169-9202
Publication date1997-07-07
First online date1998-03-26
Abstract

The diastereoselective synthesis of (−)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C4–C8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield.

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Citation (ISO format)
DE BRABANDER, Jef, VON OPPOLZER, Wolfgang. Enantioselective total synthesis of (−)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step. In: Tetrahedron, 1997, vol. 53, n° 27, p. 9169–9202. doi: 10.1016/s0040-4020(97)00617-0
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ISSN of the journal0040-4020
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