Enantioselective total synthesis of (-)-dactylolide

Ignace Louis; Natasha L. Hungerford; Edward J. Humphries; Malcolm D. McLeod

doi:10.1021/ol053092b

Enantioselective total synthesis of (-)-dactylolide

Ignace Louis, Natasha L. Hungerford, Edward J. Humphries, Malcolm D. McLeod^*

^*Corresponding author for this work

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

55 Citations (Scopus)

Abstract

The enantioselective total synthesis of (-)-dactylolide is reported. The absolute stereochemistry of the tetrahydropyran was established by catalytic asymmetric Jacobsen hetero-Diels-Alder reaction. The remote C19 stereocenter was introduced by a sequence of chelation-controlled Grignard addition and Ireland-Claisen rearrangement.

Original language	English
Pages (from-to)	1117-1120
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	6
DOIs	https://doi.org/10.1021/ol053092b
Publication status	Published - 16 Mar 2006
Externally published	Yes

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10.1021/ol053092b

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title = "Enantioselective total synthesis of (-)-dactylolide",

abstract = "The enantioselective total synthesis of (-)-dactylolide is reported. The absolute stereochemistry of the tetrahydropyran was established by catalytic asymmetric Jacobsen hetero-Diels-Alder reaction. The remote C19 stereocenter was introduced by a sequence of chelation-controlled Grignard addition and Ireland-Claisen rearrangement.",

author = "Ignace Louis and Hungerford, {Natasha L.} and Humphries, {Edward J.} and McLeod, {Malcolm D.}",

year = "2006",

month = mar,

day = "16",

doi = "10.1021/ol053092b",

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volume = "8",

pages = "1117--1120",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Enantioselective total synthesis of (-)-dactylolide

AU - Louis, Ignace

AU - Hungerford, Natasha L.

AU - Humphries, Edward J.

AU - McLeod, Malcolm D.

PY - 2006/3/16

Y1 - 2006/3/16

N2 - The enantioselective total synthesis of (-)-dactylolide is reported. The absolute stereochemistry of the tetrahydropyran was established by catalytic asymmetric Jacobsen hetero-Diels-Alder reaction. The remote C19 stereocenter was introduced by a sequence of chelation-controlled Grignard addition and Ireland-Claisen rearrangement.

AB - The enantioselective total synthesis of (-)-dactylolide is reported. The absolute stereochemistry of the tetrahydropyran was established by catalytic asymmetric Jacobsen hetero-Diels-Alder reaction. The remote C19 stereocenter was introduced by a sequence of chelation-controlled Grignard addition and Ireland-Claisen rearrangement.

UR - http://www.scopus.com/inward/record.url?scp=33646454422&partnerID=8YFLogxK

U2 - 10.1021/ol053092b

DO - 10.1021/ol053092b

M3 - Article

SN - 1523-7060

VL - 8

SP - 1117

EP - 1120

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Enantioselective total synthesis of (-)-dactylolide

Abstract

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