Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides: Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate

P. E. Maligres; V. Upadhyay; K. Rossen; S. J. Cianciosi; R. M. Purick; K. K. Eng; R. A. Reamer; D. Askin; R. P. Volante; P. J. Reider

doi:10.1016/0040-4039(95)00273-F

Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides: Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate

P. E. Maligres
, V. Upadhyay
, K. Rossen
, S. J. Cianciosi
, R. M. Purick
, K. K. Eng
, R. A. Reamer
, D. Askin
, R. P. Volante
, P. J. Reider

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

73 Scopus citations

Abstract

Reaction of 2-alkyl-4-enamides 2, 9-15 with NIS and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins 3, 16-22 with essentially no iodolactone by-product. This methodology has been successfully employed for the synthesis of the epoxide intermediate 4 of the orally active Merck HIV-1 protease inhibitor L-735,524.

Original language	English (US)
Pages (from-to)	2195-2198
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	13
DOIs	https://doi.org/10.1016/0040-4039(95)00273-F
State	Published - Mar 27 1995
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(95)00273-F

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Maligres, P. E., Upadhyay, V., Rossen, K., Cianciosi, S. J., Purick, R. M., Eng, K. K., Reamer, R. A., Askin, D., Volante, R. P., & Reider, P. J. (1995). Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides: Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate. Tetrahedron Letters, 36(13), 2195-2198. https://doi.org/10.1016/0040-4039(95)00273-F

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title = "Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides: Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate",

abstract = "Reaction of 2-alkyl-4-enamides 2, 9-15 with NIS and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins 3, 16-22 with essentially no iodolactone by-product. This methodology has been successfully employed for the synthesis of the epoxide intermediate 4 of the orally active Merck HIV-1 protease inhibitor L-735,524.",

author = "Maligres, \{P. E.\} and V. Upadhyay and K. Rossen and Cianciosi, \{S. J.\} and Purick, \{R. M.\} and Eng, \{K. K.\} and Reamer, \{R. A.\} and D. Askin and Volante, \{R. P.\} and Reider, \{P. J.\}",

year = "1995",

month = mar,

day = "27",

doi = "10.1016/0040-4039(95)00273-F",

language = "English (US)",

volume = "36",

pages = "2195--2198",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "13",

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TY - JOUR

T1 - Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides

T2 - Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate

AU - Maligres, P. E.

AU - Upadhyay, V.

AU - Rossen, K.

AU - Cianciosi, S. J.

AU - Purick, R. M.

AU - Eng, K. K.

AU - Reamer, R. A.

AU - Askin, D.

AU - Volante, R. P.

AU - Reider, P. J.

PY - 1995/3/27

Y1 - 1995/3/27

N2 - Reaction of 2-alkyl-4-enamides 2, 9-15 with NIS and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins 3, 16-22 with essentially no iodolactone by-product. This methodology has been successfully employed for the synthesis of the epoxide intermediate 4 of the orally active Merck HIV-1 protease inhibitor L-735,524.

AB - Reaction of 2-alkyl-4-enamides 2, 9-15 with NIS and aqueous sodium bicarbonate results in the diastereoselective formation of the corresponding iodohydrins 3, 16-22 with essentially no iodolactone by-product. This methodology has been successfully employed for the synthesis of the epoxide intermediate 4 of the orally active Merck HIV-1 protease inhibitor L-735,524.

UR - https://www.scopus.com/pages/publications/0028967188

UR - https://www.scopus.com/pages/publications/0028967188#tab=citedBy

U2 - 10.1016/0040-4039(95)00273-F

DO - 10.1016/0040-4039(95)00273-F

M3 - Article

AN - SCOPUS:0028967188

SN - 0040-4039

VL - 36

SP - 2195

EP - 2198

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 13

ER -

Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides: Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate

Abstract

All Science Journal Classification (ASJC) codes

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