Stereoselective Grignard additions to N-formyl hydrazone: a concise synthesis of Noxafil(R) side chain and a synthesis of Noxafil(R) | Health & Environmental Research Online (HERO)

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Citation
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HERO ID

7450235

Reference Type

Journal Article

Title

Stereoselective Grignard additions to N-formyl hydrazone: a concise synthesis of Noxafil(R) side chain and a synthesis of Noxafil(R)

Author(s)

Saksena, AK; Girijavallabhan, VM; Wang, HY; Lovey, RG; Guenter, F; Mergelsberg, I; Puar, MS

Year

2004

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Journal

Tetrahedron Letters
ISSN: 0040-4039
EISSN: 1873-3581

Volume

Issue

Page Numbers

8249-8251

Language

English

DOI

10.1016/j.tetlet.2004.09.028

Web of Science Id

WOS:000224517600028

URL

https://linkinghub.elsevier.com/retrieve/pii/S0040403904019690
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Abstract

Addition of ethyl Grignard reagent to the formyl hydrazone 11 via in situ silylation provided the corresponding formyl hydrazine with excellent diastereoselectivity in favor of the desired S,S-diastereoisomer 6. Treatment of 6 with the phenyl carbamate 13 efficiently provided the O-benzyl protected Noxafil, which was deprotected to provide NoxafilR. Â© 2004 Elsevier Ltd. All rights reserved.

Keywords

antifungal agent; carbamic acid derivative; hydrazone derivative; posaconazole; article; chemical reaction; diastereoisomer; drug synthesis; Grignard reaction; reaction analysis; stereochemistry