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Diastereoselective conjugate addition of lithium methylcyanocuprate to the chiral isoprene units 2-(R)- and (S)-benzyloxy-2,5-dihydro-4-furancarboxaldehyde. Total synthesis of (-)- and (+)-botryodiplodin and (+)- and (-)-epibotryodiplodin.

Rehnberg, Nicola LU orcid ; Frejd, Torbjörn LU and Magnusson, Göran LU (1987) In Tetrahedron Letters 28(31). p.3589-3592
Abstract
Conjugate addition of lithium methylcyanocuprate to the titlealdehydes proceeded with high diastereoselectivity (d.e. 94%). Methyl lithium 1,2-addition, followed by Swern oxidation of the resultingalcohols, gave benzyl botryodiplodin and benzyl epi-botryodiplodin.Hydrogenolysis of the benzyl groups gave the enantiomeric pairs ofbotryodiplodin 10r and 10s and epi-botryodiplodin (9r and 9s).
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author
; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron Letters
volume
28
issue
31
pages
4 pages
publisher
Elsevier
external identifiers
  • scopus:0001314937
ISSN
0040-4039
DOI
10.1016/S0040-4039(00)95543-6
language
English
LU publication?
yes
id
d9966446-8c67-4230-9a6c-801cb7245783
date added to LUP
2021-11-11 11:29:49
date last changed
2021-11-12 04:00:56
@article{d9966446-8c67-4230-9a6c-801cb7245783,
  abstract     = {{Conjugate addition of lithium methylcyanocuprate to the titlealdehydes proceeded with high diastereoselectivity (d.e. 94%). Methyl lithium 1,2-addition, followed by Swern oxidation of the resultingalcohols, gave benzyl botryodiplodin and benzyl epi-botryodiplodin.Hydrogenolysis of the benzyl groups gave the enantiomeric pairs ofbotryodiplodin 10r and 10s and epi-botryodiplodin (9r and 9s).}},
  author       = {{Rehnberg, Nicola and Frejd, Torbjörn and Magnusson, Göran}},
  issn         = {{0040-4039}},
  language     = {{eng}},
  number       = {{31}},
  pages        = {{3589--3592}},
  publisher    = {{Elsevier}},
  series       = {{Tetrahedron Letters}},
  title        = {{Diastereoselective conjugate addition of lithium methylcyanocuprate to the chiral isoprene units 2-(R)- and (S)-benzyloxy-2,5-dihydro-4-furancarboxaldehyde. Total synthesis of (-)- and (+)-botryodiplodin and (+)- and (-)-epibotryodiplodin.}},
  url          = {{http://dx.doi.org/10.1016/S0040-4039(00)95543-6}},
  doi          = {{10.1016/S0040-4039(00)95543-6}},
  volume       = {{28}},
  year         = {{1987}},
}