The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers

Autor:	Ajit S. Borhade, Yunnus B. Shaikh, Sanjay W. Chavhan, Attrimuni P. Dhondge, Deekshaputra R. Birhade, Ramesh Gannimani, Mayur P. Desai, Nagorao R. Dhatrak, Mukund G. Kulkarni
Rok vydání:	2010
Předmět:	Stereochemistry Organic Chemistry Catalysis Inorganic Chemistry chemistry.chemical_compound chemistry Furan Glyceraldehyde Wittig reaction medicine Moiety Stereoselectivity Physical and Theoretical Chemistry Chirality (chemistry) Derivative (chemistry) Darunavir medicine.drug
Zdroj:	Tetrahedron: Asymmetry. 21:2394-2398
ISSN:	0957-4166
DOI:	10.1016/j.tetasy.2010.08.005
Popis:	The stereoselective synthesis of all the possible stereoisomers of bis-tetrahydrofyran alcohol, a ligand used for obtaining HIV protease inhibitors including Darunavir 1 and Brecanavir 2 has been achieved. A key intermediate 4-pentenal 5 was obtained by employing a Wittig olefination-Claisen rearrangement protocol from d -glyceraldehyde derivative 3 as a source of chirality. The 4-pentenal was readily converted in the bis-THF alcohol moiety in three steps.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f0d240a06d058f50b1a381709adaf590 https://doi.org/10.1016/j.tetasy.2010.08.005 Zobrazit plný text záznamu Full Text from ScienceDirect