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Synthetic Studies Toward the Crassifoside F: Synthesis of Oxygen‐Rich Bicyclic Core
Author(s) -
Maurya Sushil K.
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600515
Subject(s) - chemistry , natural product , intramolecular force , orthoester , bicyclic molecule , sn2 reaction , stereochemistry , propargyl , ring (chemistry) , combinatorial chemistry , catalysis , organic chemistry
Abstract An approach to the total synthesis of crassifoside F, a natural product isolated from Curculigo crassifolia with ACE (angiotensin‐converting enzyme) inhibitory activity, has been developed. An intramolecular S N 2 reaction has been employed as the key reaction to construct the central oxygen rich core. The glucosyl‐fused eight‐membered cyclic skeleton present in this natural product is unique and has been formed via a Au I catalyzed novel glycosidation reaction using a 1,2‐propargyl orthoester and different asymmetric reactions. Moreover, this ring has been selected as a handle to control the stereochemistry.