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Total synthesis of the lignans (-)- and (+)-burseran, (-)-cubebin, and (-)-hinokinin by diastereoselective conjugate addition of benzyl anions to 2-(R) and (s)-benzyloxy-2,5-dihydro-4-(3,4-methylenedioxybenzoyl)furan

Rehnberg, Nicola LU orcid and Magnusson, Göran LU (1988) In Tetrahedron Letters 29(29). p.3599-3602
Abstract

1,2-Addition of 3,4-methylenedioxymagnesium bromide to 2-(R) and (S)-benzyloxy-2,5-dihydro-4-furancarboxaldehyde, followed by oxidation, gave the title ketones (3r and 3s). Conjugate addition of the anions of 3,4,5-trimethoxy- and 3,4-methylenedioxybenzaldehyde diphenylthioacetal to 3r and 3s and Raney-nickel desulfurisation, followed by hydrogenolysis under various conditions, gave the title lignans. (-)-Burseran was prepared in >98% diastereomeric excess.

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author
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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron Letters
volume
29
issue
29
pages
4 pages
publisher
Elsevier
external identifiers
  • scopus:0023710199
ISSN
0040-4039
DOI
10.1016/0040-4039(88)85304-8
language
English
LU publication?
yes
additional info
Funding Information: AcknowledPments: We thank M. Levin for technicala ssistanceT. his work was supportedb y the Swedish Natural Science ResearchC ouncil and the SwedishN ational Board for Technical Development.
id
6ff5a5f0-5ea3-48b8-bbe2-34268c39229b
date added to LUP
2021-11-11 11:40:42
date last changed
2025-10-14 11:41:48
@article{6ff5a5f0-5ea3-48b8-bbe2-34268c39229b,
  abstract     = {{<p>1,2-Addition of 3,4-methylenedioxymagnesium bromide to 2-(R) and (S)-benzyloxy-2,5-dihydro-4-furancarboxaldehyde, followed by oxidation, gave the title ketones (3r and 3s). Conjugate addition of the anions of 3,4,5-trimethoxy- and 3,4-methylenedioxybenzaldehyde diphenylthioacetal to 3r and 3s and Raney-nickel desulfurisation, followed by hydrogenolysis under various conditions, gave the title lignans. (-)-Burseran was prepared in &gt;98% diastereomeric excess.</p>}},
  author       = {{Rehnberg, Nicola and Magnusson, Göran}},
  issn         = {{0040-4039}},
  language     = {{eng}},
  number       = {{29}},
  pages        = {{3599--3602}},
  publisher    = {{Elsevier}},
  series       = {{Tetrahedron Letters}},
  title        = {{Total synthesis of the lignans (-)- and (+)-burseran, (-)-cubebin, and (-)-hinokinin by diastereoselective conjugate addition of benzyl anions to 2-(R) and (s)-benzyloxy-2,5-dihydro-4-(3,4-methylenedioxybenzoyl)furan}},
  url          = {{http://dx.doi.org/10.1016/0040-4039(88)85304-8}},
  doi          = {{10.1016/0040-4039(88)85304-8}},
  volume       = {{29}},
  year         = {{1988}},
}