Total Synthesis of Incarviditone and Incarvilleatone

Andrew Lawrence; Patrick D. Brown; Anthony C. Willis; Michael S. Sherburn

doi:10.1021/ol302042u

Total Synthesis of Incarviditone and Incarvilleatone

Andrew Lawrence, Patrick D. Brown, Anthony C. Willis, Michael S. Sherburn

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

Abstract / Description of output

The total synthesis of the racemic natural products (±)-incarviditone and (±)-incarvilleatone has been accomplished in three steps via biomimetic dimerization of (±)-rengyolone. Homochiral dimerization of (±)-rengyolone affords (±)-incarviditone through a domino oxa-Michael/Michael sequence. Heterochiral dimerization, involving a domino oxa-Michael/Michael/aldol reaction sequence, affords (±)-incarvilleatone. Single-crystal X-ray analysis of a derivative of (±)-incarviditone has resulted in revision of the originally proposed structure.

Original language	English
Pages (from-to)	4537–4539
Journal	Organic letters
Volume	14
Issue number	17
Early online date	29 Aug 2012
DOIs	https://doi.org/10.1021/ol302042u
Publication status	Published - 7 Sept 2012

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title = "Total Synthesis of Incarviditone and Incarvilleatone",

abstract = "The total synthesis of the racemic natural products (±)-incarviditone and (±)-incarvilleatone has been accomplished in three steps via biomimetic dimerization of (±)-rengyolone. Homochiral dimerization of (±)-rengyolone affords (±)-incarviditone through a domino oxa-Michael/Michael sequence. Heterochiral dimerization, involving a domino oxa-Michael/Michael/aldol reaction sequence, affords (±)-incarvilleatone. Single-crystal X-ray analysis of a derivative of (±)-incarviditone has resulted in revision of the originally proposed structure.",

author = "Andrew Lawrence and Brown, {Patrick D.} and Willis, {Anthony C.} and Sherburn, {Michael S.}",

year = "2012",

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language = "English",

volume = "14",

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journal = "Organic letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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T1 - Total Synthesis of Incarviditone and Incarvilleatone

AU - Lawrence, Andrew

AU - Brown, Patrick D.

AU - Willis, Anthony C.

AU - Sherburn, Michael S.

PY - 2012/9/7

Y1 - 2012/9/7

N2 - The total synthesis of the racemic natural products (±)-incarviditone and (±)-incarvilleatone has been accomplished in three steps via biomimetic dimerization of (±)-rengyolone. Homochiral dimerization of (±)-rengyolone affords (±)-incarviditone through a domino oxa-Michael/Michael sequence. Heterochiral dimerization, involving a domino oxa-Michael/Michael/aldol reaction sequence, affords (±)-incarvilleatone. Single-crystal X-ray analysis of a derivative of (±)-incarviditone has resulted in revision of the originally proposed structure.

AB - The total synthesis of the racemic natural products (±)-incarviditone and (±)-incarvilleatone has been accomplished in three steps via biomimetic dimerization of (±)-rengyolone. Homochiral dimerization of (±)-rengyolone affords (±)-incarviditone through a domino oxa-Michael/Michael sequence. Heterochiral dimerization, involving a domino oxa-Michael/Michael/aldol reaction sequence, affords (±)-incarvilleatone. Single-crystal X-ray analysis of a derivative of (±)-incarviditone has resulted in revision of the originally proposed structure.

U2 - 10.1021/ol302042u

DO - 10.1021/ol302042u

M3 - Article

AN - SCOPUS:84866019504

SN - 1523-7060

VL - 14

SP - 4537

EP - 4539

JO - Organic letters

JF - Organic letters

IS - 17

ER -

Total Synthesis of Incarviditone and Incarvilleatone

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