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

72 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

Access to Document

10.1016/0040-4039(95)00273-F

Cite this

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

@article{9aab4b0c15c541fab3e314570fddd1a8,

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",

}

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/inward/citedby.url?scp=0028967188&partnerID=8YFLogxK

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

Access to Document

Other files and links

Fingerprint

Cite this