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
(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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https://lup.lub.lu.se/record/6ff5a5f0-5ea3-48b8-bbe2-34268c39229b
- author
- Rehnberg, Nicola LU and Magnusson, Göran LU
- organization
- publishing date
- 1988
- 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
- 2021-11-13 02:25:55
@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 >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}}, }