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

Cite this

@article{a6d5426db1534054920ed9ce1ead6b09,

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",

}

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/pages/publications/0030851241#tab=citedBy

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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