Total Synthesis of (-)-Maysine

A. I. Meyers; Kevin A. Babiak; Arthur L. Campbell; Daniel L. Comins; Michael P. Fleming; Rainer Henning; Manfred Heuschmann; James P. Hudspeth; John M. Kane; Paul J. Reider; Dennis M. Roland; Kimihiro Shimizu; Kyoshi Tomioka; Robert D. Walkup

doi:10.1021/ja00353a027

Total Synthesis of (-)-Maysine

A. I. Meyers, Kevin A. Babiak, Arthur L. Campbell, Daniel L. Comins, Michael P. Fleming, Rainer Henning, Manfred Heuschmann, James P. Hudspeth, John M. Kane, Paul J. Reider, Dennis M. Roland, Kimihiro Shimizu, Kyoshi Tomioka, Robert D. Walkup

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

80 Scopus citations

Abstract

A convergent synthesis of the natural macrocycle (-)-maysine (3) has been accomplished involving only a single separation of epimers at C-10. The scheme involved the preparation of three major fragments: (a) the western zone, 4; (b) the southern zone, 6; and (c) the northeastern zone in enantiomerically pure from (+)-37. Each of these components was coupled through the appropriate functionality leading to the target compound.

Original language	English (US)
Pages (from-to)	5015-5024
Number of pages	10
Journal	Journal of the American Chemical Society
Volume	105
Issue number	15
DOIs	https://doi.org/10.1021/ja00353a027
State	Published - Jul 1983
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00353a027

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@article{7d181daa28a24c20960c357c25a2665c,

title = "Total Synthesis of (-)-Maysine",

abstract = "A convergent synthesis of the natural macrocycle (-)-maysine (3) has been accomplished involving only a single separation of epimers at C-10. The scheme involved the preparation of three major fragments: (a) the western zone, 4; (b) the southern zone, 6; and (c) the northeastern zone in enantiomerically pure from (+)-37. Each of these components was coupled through the appropriate functionality leading to the target compound.",

author = "Meyers, {A. I.} and Babiak, {Kevin A.} and Campbell, {Arthur L.} and Comins, {Daniel L.} and Fleming, {Michael P.} and Rainer Henning and Manfred Heuschmann and Hudspeth, {James P.} and Kane, {John M.} and Reider, {Paul J.} and Roland, {Dennis M.} and Kimihiro Shimizu and Kyoshi Tomioka and Walkup, {Robert D.}",

year = "1983",

month = jul,

doi = "10.1021/ja00353a027",

language = "English (US)",

volume = "105",

pages = "5015--5024",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "15",

}

TY - JOUR

T1 - Total Synthesis of (-)-Maysine

AU - Meyers, A. I.

AU - Babiak, Kevin A.

AU - Campbell, Arthur L.

AU - Comins, Daniel L.

AU - Fleming, Michael P.

AU - Henning, Rainer

AU - Heuschmann, Manfred

AU - Hudspeth, James P.

AU - Kane, John M.

AU - Reider, Paul J.

AU - Roland, Dennis M.

AU - Shimizu, Kimihiro

AU - Tomioka, Kyoshi

AU - Walkup, Robert D.

PY - 1983/7

Y1 - 1983/7

N2 - A convergent synthesis of the natural macrocycle (-)-maysine (3) has been accomplished involving only a single separation of epimers at C-10. The scheme involved the preparation of three major fragments: (a) the western zone, 4; (b) the southern zone, 6; and (c) the northeastern zone in enantiomerically pure from (+)-37. Each of these components was coupled through the appropriate functionality leading to the target compound.

AB - A convergent synthesis of the natural macrocycle (-)-maysine (3) has been accomplished involving only a single separation of epimers at C-10. The scheme involved the preparation of three major fragments: (a) the western zone, 4; (b) the southern zone, 6; and (c) the northeastern zone in enantiomerically pure from (+)-37. Each of these components was coupled through the appropriate functionality leading to the target compound.

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U2 - 10.1021/ja00353a027

DO - 10.1021/ja00353a027

M3 - Article

AN - SCOPUS:0020786939

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VL - 105

SP - 5015

EP - 5024

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 15

ER -

Total Synthesis of (-)-Maysine

Abstract

All Science Journal Classification (ASJC) codes

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