Total synthesis of incarviditone and incarvilleatone

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

doi:10.1021/ol302042u

Total synthesis of incarviditone and incarvilleatone

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

^*Corresponding author for this work

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

53 Citations (Scopus)

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.

Original language	English
Pages (from-to)	4537-4539
Number of pages	3
Journal	Organic Letters
Volume	14
Issue number	17
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 = "Brown, {Patrick D.} and Willis, {Anthony C.} and Sherburn, {Michael S.} and Lawrence, {Andrew L.}",

year = "2012",

month = sep,

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language = "English",

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journal = "Organic Letters",

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T1 - Total synthesis of incarviditone and incarvilleatone

AU - Brown, Patrick D.

AU - Willis, Anthony C.

AU - Sherburn, Michael S.

AU - Lawrence, Andrew L.

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.

UR - http://www.scopus.com/inward/record.url?scp=84866019504&partnerID=8YFLogxK

U2 - 10.1021/ol302042u

DO - 10.1021/ol302042u

M3 - Article

SN - 1523-7060

VL - 14

SP - 4537

EP - 4539

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Total synthesis of incarviditone and incarvilleatone

Abstract

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