Synthesis of the fused bicyclic lactam-lactone terminus of neooxazolomycin by a novel dianion cyclocondensation

Andrew S. Kende; Robert J. DeVita

doi:10.1016/S0040-4039(00)86101-8

Synthesis of the fused bicyclic lactam-lactone terminus of neooxazolomycin by a novel dianion cyclocondensation

Andrew S. Kende
, Robert J. DeVita

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

14 Scopus citations

Abstract

Reaction of the dianion (5) derived from an acylaminomalonic ester with S-(-)-MOM lactate (6) yields β-hydroxylactams 7 and 8 in a 2:1 ratio. Deprotection and lactonization of 7, followed by saponification and 2 step carboxyl reduction efficiently produces the fused bicyclic lactam-lactone 12, a chiral model of the antitumor antibiotic neooxazolomycm 1.

Original language	English
Pages (from-to)	2521-2524
Number of pages	4
Journal	Tetrahedron Letters
Volume	29
Issue number	21
DOIs	https://doi.org/10.1016/S0040-4039(00)86101-8
State	Published - 1988
Externally published	Yes

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10.1016/S0040-4039(00)86101-8

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@article{399bafe1154c4d1caa4e4544e68db910,

title = "Synthesis of the fused bicyclic lactam-lactone terminus of neooxazolomycin by a novel dianion cyclocondensation",

abstract = "Reaction of the dianion (5) derived from an acylaminomalonic ester with S-(-)-MOM lactate (6) yields β-hydroxylactams 7 and 8 in a 2:1 ratio. Deprotection and lactonization of 7, followed by saponification and 2 step carboxyl reduction efficiently produces the fused bicyclic lactam-lactone 12, a chiral model of the antitumor antibiotic neooxazolomycm 1.",

author = "Kende, \{Andrew S.\} and DeVita, \{Robert J.\}",

note = "Funding Information: ACKNOWLEDGMENT8 Partial support of this rwearch by grant CA 18846,a warded by the National Cancer Institute,N E-USPHS, is gratefully acknowledged.R JD thanks the University of Rochesterf or financial support in the form of a ShermanC larke FeIlowship.",

year = "1988",

doi = "10.1016/S0040-4039(00)86101-8",

language = "English",

volume = "29",

pages = "2521--2524",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "21",

}

TY - JOUR

T1 - Synthesis of the fused bicyclic lactam-lactone terminus of neooxazolomycin by a novel dianion cyclocondensation

AU - Kende, Andrew S.

AU - DeVita, Robert J.

N1 - Funding Information: ACKNOWLEDGMENT8 Partial support of this rwearch by grant CA 18846,a warded by the National Cancer Institute,N E-USPHS, is gratefully acknowledged.R JD thanks the University of Rochesterf or financial support in the form of a ShermanC larke FeIlowship.

PY - 1988

Y1 - 1988

N2 - Reaction of the dianion (5) derived from an acylaminomalonic ester with S-(-)-MOM lactate (6) yields β-hydroxylactams 7 and 8 in a 2:1 ratio. Deprotection and lactonization of 7, followed by saponification and 2 step carboxyl reduction efficiently produces the fused bicyclic lactam-lactone 12, a chiral model of the antitumor antibiotic neooxazolomycm 1.

AB - Reaction of the dianion (5) derived from an acylaminomalonic ester with S-(-)-MOM lactate (6) yields β-hydroxylactams 7 and 8 in a 2:1 ratio. Deprotection and lactonization of 7, followed by saponification and 2 step carboxyl reduction efficiently produces the fused bicyclic lactam-lactone 12, a chiral model of the antitumor antibiotic neooxazolomycm 1.

UR - https://www.scopus.com/pages/publications/0023936505

U2 - 10.1016/S0040-4039(00)86101-8

DO - 10.1016/S0040-4039(00)86101-8

M3 - Article

AN - SCOPUS:0023936505

SN - 0040-4039

VL - 29

SP - 2521

EP - 2524

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

Synthesis of the fused bicyclic lactam-lactone terminus of neooxazolomycin by a novel dianion cyclocondensation

Abstract

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