Synthesis of the orally active spiroindoline-based Growth Hormone Secretagogue, MK-677

Peter E. Maligres; Ioannis Houpis; Kai Rossen; Audrey Molina; Jess Sager; Veena Upadhyay; Kenneth M. Wells; Robert A. Reamer; Joseph E. Lynch; David Askin; R. P. Volante; Paul J. Reider; Peter Houghton

doi:10.1016/S0040-4020(97)00359-1

Synthesis of the orally active spiroindoline-based Growth Hormone Secretagogue, MK-677

Peter E. Maligres, Ioannis Houpis, Kai Rossen, Audrey Molina, Jess Sager, Veena Upadhyay, Kenneth M. Wells, Robert A. Reamer, Joseph E. Lynch, David Askin, R. P. Volante, Paul J. Reider, Peter Houghton

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

55 Scopus citations

Abstract

The preparation of the Merck Growth Hormone Secretagogue; MK-677 is described. A Fischer indole/reduction based strategy provides the novel spiroindoline nucleus of this potent compound. This optimized sequence necessitates the isolation of only one intermediate 10 and provides MK-677 in 48% overall yield from isonipecotic acid 3.

Original language	English (US)
Pages (from-to)	10983-10992
Number of pages	10
Journal	Tetrahedron
Volume	53
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4020(97)00359-1
State	Published - Aug 11 1997
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Fischer indole
Growth hormone secretagogue
MK-677
Rosenmund
Spiroindoline

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10.1016/S0040-4020(97)00359-1

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title = "Synthesis of the orally active spiroindoline-based Growth Hormone Secretagogue, MK-677",

abstract = "The preparation of the Merck Growth Hormone Secretagogue; MK-677 is described. A Fischer indole/reduction based strategy provides the novel spiroindoline nucleus of this potent compound. This optimized sequence necessitates the isolation of only one intermediate 10 and provides MK-677 in 48\% overall yield from isonipecotic acid 3.",

keywords = "Fischer indole, Growth hormone secretagogue, MK-677, Rosenmund, Spiroindoline",

author = "Maligres, \{Peter E.\} and Ioannis Houpis and Kai Rossen and Audrey Molina and Jess Sager and Veena Upadhyay and Wells, \{Kenneth M.\} and Reamer, \{Robert A.\} and Lynch, \{Joseph E.\} and David Askin and Volante, \{R. P.\} and Reider, \{Paul J.\} and Peter Houghton",

year = "1997",

month = aug,

day = "11",

doi = "10.1016/S0040-4020(97)00359-1",

language = "English (US)",

volume = "53",

pages = "10983--10992",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "32",

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TY - JOUR

T1 - Synthesis of the orally active spiroindoline-based Growth Hormone Secretagogue, MK-677

AU - Maligres, Peter E.

AU - Houpis, Ioannis

AU - Rossen, Kai

AU - Molina, Audrey

AU - Sager, Jess

AU - Upadhyay, Veena

AU - Wells, Kenneth M.

AU - Reamer, Robert A.

AU - Lynch, Joseph E.

AU - Askin, David

AU - Volante, R. P.

AU - Reider, Paul J.

AU - Houghton, Peter

PY - 1997/8/11

Y1 - 1997/8/11

N2 - The preparation of the Merck Growth Hormone Secretagogue; MK-677 is described. A Fischer indole/reduction based strategy provides the novel spiroindoline nucleus of this potent compound. This optimized sequence necessitates the isolation of only one intermediate 10 and provides MK-677 in 48% overall yield from isonipecotic acid 3.

AB - The preparation of the Merck Growth Hormone Secretagogue; MK-677 is described. A Fischer indole/reduction based strategy provides the novel spiroindoline nucleus of this potent compound. This optimized sequence necessitates the isolation of only one intermediate 10 and provides MK-677 in 48% overall yield from isonipecotic acid 3.

KW - Fischer indole

KW - Growth hormone secretagogue

KW - MK-677

KW - Rosenmund

KW - Spiroindoline

UR - https://www.scopus.com/pages/publications/0030851241

UR - https://www.scopus.com/inward/citedby.url?scp=0030851241&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(97)00359-1

DO - 10.1016/S0040-4020(97)00359-1

M3 - Article

AN - SCOPUS:0030851241

SN - 0040-4020

VL - 53

SP - 10983

EP - 10992

JO - Tetrahedron

JF - Tetrahedron

IS - 32

ER -

Synthesis of the orally active spiroindoline-based Growth Hormone Secretagogue, MK-677

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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