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

85 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.

UR - https://www.scopus.com/pages/publications/0020786939

UR - https://www.scopus.com/pages/publications/0020786939#tab=citedBy

U2 - 10.1021/ja00353a027

DO - 10.1021/ja00353a027

M3 - Article

AN - SCOPUS:0020786939

SN - 0002-7863

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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