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Total Synthesis of 3‐ O ‐Benzyl‐1,3,5‐tri‐ epi ‐calystegine B 2 from L ‐Sorbose
Author(s) -
Lo Re Daniele,
Franco Francisco,
SánchezCantalejo Fernando,
Tamayo Juan A.
Publication year - 2009
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.200801232
Subject(s) - chemistry , wittig reaction , octane , derivative (finance) , ring closing metathesis , alkylation , stereochemistry , tropane , metathesis , total synthesis , medicinal chemistry , organic chemistry , catalysis , financial economics , economics , polymerization , polymer
The well known 2,3:4,6‐di‐ O ‐isopropylidene‐α‐ L ‐sorbofuranose ( 12 ) was chosen as starting material for the synthesis of (1 S ,4 R ,5 S ,6 S ,7 S )‐4‐amino‐6‐benzyloxy‐1,7‐isopropylidenedioxy‐8‐oxabicyclo[3.2.1]octane ( 33 ) and (1 S ,4 S ,5 S ,6 S ,7 S )‐4‐amino‐6‐benzyloxy‐1,7‐isopropylidenedioxy‐8‐oxabicyclo[3.2.1]octane ( 34 ) through carbon chain‐lengthening at C‐1 and C‐6 by Wittig and magnesium‐mediated alkylation methodology, respectively, followed by ring‐closing olefin metathesis (RCM). These promising oxabicyclic compounds were key intermediates for the preparation of the polyhydroxylated nor ‐tropane alkaloid 1,3,5‐tri‐ epi ‐calystegine B 2 ( 10 ) as its 3‐ O ‐benzyl derivative 35 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)