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Synthesis of the Spiroketal Fragment of (–)‐Ushikulide A
Author(s) -
Yadav Jhillu S.,
Reddy N. Mallikarjuna,
Rahman Md. Ataur,
Prasad Attaluri R.
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402196
Subject(s) - chemistry , tetrahydropyran , moiety , prins reaction , stereoselectivity , alkylation , stereochemistry , hydrolysis , derivative (finance) , isocyanide , fragment (logic) , ring (chemistry) , combinatorial chemistry , organic chemistry , catalysis , financial economics , economics , computer science , programming language
The stereoselective synthesis of the spiroketal fragment of the immunosuppressant (–)‐ushikulide A is described. The salient feature of this synthesis is the construction of the spiroketal moiety by hydrolysis of a dialkylated tosylmethyl isocyanide derivative derived from alkylation of tosylmethyl isocyanide (TosMIC) with suitably substituted halohydrin derivatives. The key functionalized tetrahydropyran ring was constructed by using Prins cyclization of the α‐acetoxy ether.