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

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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

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

Keywords

Allylboration
Asymmetric synthesis
Metathesis

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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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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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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.

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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.

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KW - Asymmetric synthesis

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

Abstract

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Keywords

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