The total synthesis of (-)-tetrahydrolipstatin

Jennifer A. Bodkin; Edward J. Humphries; Malcolm D. McLeod

doi:10.1071/CH03121

The total synthesis of (-)-tetrahydrolipstatin

Jennifer A. Bodkin
, Edward J. Humphries
, Malcolm D. McLeod^*

^*Corresponding author for this work

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

29 Citations (Scopus)

Abstract

Careful control during the bromolactonization of β,γ-unsaturated acid (4) was required to regioselectivity afford the trans-β-lactone (3) as the major diastereomer. Radical debromination of (3) followed by a three-step sequence of reactions afforded the lipase inhibitor (-)-tetrahydrolipstatin (1).

Original language	English
Pages (from-to)	795-803
Number of pages	9
Journal	Australian Journal of Chemistry
Volume	56
Issue number	8
DOIs	https://doi.org/10.1071/CH03121
Publication status	Published - 2003
Externally published	Yes

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10.1071/CH03121

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title = "The total synthesis of (-)-tetrahydrolipstatin",

abstract = "Careful control during the bromolactonization of β,γ-unsaturated acid (4) was required to regioselectivity afford the trans-β-lactone (3) as the major diastereomer. Radical debromination of (3) followed by a three-step sequence of reactions afforded the lipase inhibitor (-)-tetrahydrolipstatin (1).",

author = "Bodkin, \{Jennifer A.\} and Humphries, \{Edward J.\} and McLeod, \{Malcolm D.\}",

year = "2003",

doi = "10.1071/CH03121",

language = "English",

volume = "56",

pages = "795--803",

journal = "Australian Journal of Chemistry",

issn = "0004-9425",

publisher = "CSIRO",

number = "8",

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T1 - The total synthesis of (-)-tetrahydrolipstatin

AU - Bodkin, Jennifer A.

AU - Humphries, Edward J.

AU - McLeod, Malcolm D.

PY - 2003

Y1 - 2003

N2 - Careful control during the bromolactonization of β,γ-unsaturated acid (4) was required to regioselectivity afford the trans-β-lactone (3) as the major diastereomer. Radical debromination of (3) followed by a three-step sequence of reactions afforded the lipase inhibitor (-)-tetrahydrolipstatin (1).

AB - Careful control during the bromolactonization of β,γ-unsaturated acid (4) was required to regioselectivity afford the trans-β-lactone (3) as the major diastereomer. Radical debromination of (3) followed by a three-step sequence of reactions afforded the lipase inhibitor (-)-tetrahydrolipstatin (1).

UR - https://www.scopus.com/pages/publications/0041513417

U2 - 10.1071/CH03121

DO - 10.1071/CH03121

M3 - Article

SN - 0004-9425

VL - 56

SP - 795

EP - 803

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 8

ER -

The total synthesis of (-)-tetrahydrolipstatin

Abstract

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