Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions

P. Veeraraghavan Ramachandran; M. Venkat Ram Reddy; Herbert C. Brown

doi:10.1016/S0040-4039(99)02130-9

Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions

P. Veeraraghavan Ramachandran
, M. Venkat Ram Reddy
, Herbert C. Brown

Chemistry & Biochemistry

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

116 Scopus citations

Abstract

Acrylic esters of homoallylic alcohols prepared in 92-97% ee via the asymmetric allylboration of appropriate aldehydes with B- allyldiisopinocampheylborane, when refluxed in dichloromethane in the presence of 10 mol% of Grubbs' catalyst provided the natural enantiomers of (S)-(+)-parasorbic acid, (R)-(-)-massoia lactone, and (R)-(+)goniothalamin. (S)-(-)-Hexadecanolide was prepared by hydrogenating the corresponding lactenone synthesized using the above sequence. (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	583-586
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	5
DOIs	https://doi.org/10.1016/S0040-4039(99)02130-9
State	Published - Jan 29 2000

Bibliographical note

Funding Information:
Financial assistance from the Purdue Borane Research Fund is acknowledged.

Keywords

Allylboration
Asymmetric synthesis
Metathesis

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10.1016/S0040-4039(99)02130-9

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Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions. / Ramachandran, P. Veeraraghavan; Reddy, M. Venkat Ram; Brown, Herbert C.
In: Tetrahedron Letters, Vol. 41, No. 5, 29.01.2000, p. 583-586.

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

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title = "Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions",

abstract = "Acrylic esters of homoallylic alcohols prepared in 92-97\% ee via the asymmetric allylboration of appropriate aldehydes with B- allyldiisopinocampheylborane, when refluxed in dichloromethane in the presence of 10 mol\% of Grubbs' catalyst provided the natural enantiomers of (S)-(+)-parasorbic acid, (R)-(-)-massoia lactone, and (R)-(+)goniothalamin. (S)-(-)-Hexadecanolide was prepared by hydrogenating the corresponding lactenone synthesized using the above sequence. (C) 2000 Elsevier Science Ltd.",

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author = "Ramachandran, \{P. Veeraraghavan\} and Reddy, \{M. Venkat Ram\} and Brown, \{Herbert C.\}",

note = "Funding Information: Financial assistance from the Purdue Borane Research Fund is acknowledged. ",

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doi = "10.1016/S0040-4039(99)02130-9",

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T1 - Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions

AU - Ramachandran, P. Veeraraghavan

AU - Reddy, M. Venkat Ram

AU - Brown, Herbert C.

N1 - Funding Information: Financial assistance from the Purdue Borane Research Fund is acknowledged.

PY - 2000/1/29

Y1 - 2000/1/29

N2 - Acrylic esters of homoallylic alcohols prepared in 92-97% ee via the asymmetric allylboration of appropriate aldehydes with B- allyldiisopinocampheylborane, when refluxed in dichloromethane in the presence of 10 mol% of Grubbs' catalyst provided the natural enantiomers of (S)-(+)-parasorbic acid, (R)-(-)-massoia lactone, and (R)-(+)goniothalamin. (S)-(-)-Hexadecanolide was prepared by hydrogenating the corresponding lactenone synthesized using the above sequence. (C) 2000 Elsevier Science Ltd.

AB - Acrylic esters of homoallylic alcohols prepared in 92-97% ee via the asymmetric allylboration of appropriate aldehydes with B- allyldiisopinocampheylborane, when refluxed in dichloromethane in the presence of 10 mol% of Grubbs' catalyst provided the natural enantiomers of (S)-(+)-parasorbic acid, (R)-(-)-massoia lactone, and (R)-(+)goniothalamin. (S)-(-)-Hexadecanolide was prepared by hydrogenating the corresponding lactenone synthesized using the above sequence. (C) 2000 Elsevier Science Ltd.

KW - Allylboration

KW - Asymmetric synthesis

KW - Metathesis

UR - https://www.scopus.com/pages/publications/0034728178

UR - https://www.scopus.com/pages/publications/0034728178#tab=citedBy

U2 - 10.1016/S0040-4039(99)02130-9

DO - 10.1016/S0040-4039(99)02130-9

M3 - Article

AN - SCOPUS:0034728178

SN - 0040-4039

VL - 41

SP - 583

EP - 586

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 5

ER -

Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions

Abstract

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