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

Nicola Rehnberg; Göran Magnusson

doi:10.1016/0040-4039(88)85304-8

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

Nicola Rehnberg, Göran Magnusson

Centre for Analysis and Synthesis

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	3599-3602
Number of pages	4
Journal	Tetrahedron Letters
Volume	29
Issue number	29
DOIs	https://doi.org/10.1016/0040-4039(88)85304-8
Publication status	Published - 1988

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Organic Chemistry

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10.1016/0040-4039(88)85304-8

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@article{6ff5a5f05ea348b8bbe234268c39229b,

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",

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.",

author = "Nicola Rehnberg and G{\"o}ran Magnusson",

note = "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.",

year = "1988",

doi = "10.1016/0040-4039(88)85304-8",

language = "English",

volume = "29",

pages = "3599--3602",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier",

number = "29",

}

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; Magnusson, Göran.
In: Tetrahedron Letters, Vol. 29, No. 29, 1988, p. 3599-3602.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - 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

AU - Rehnberg, Nicola

AU - Magnusson, Göran

N1 - 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.

PY - 1988

Y1 - 1988

N2 - 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.

AB - 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.

U2 - 10.1016/0040-4039(88)85304-8

DO - 10.1016/0040-4039(88)85304-8

M3 - Article

AN - SCOPUS:0023710199

SN - 0040-4039

VL - 29

SP - 3599

EP - 3602

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 29

ER -