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Exploration of High‐Pressure Cycloadducts of Furans and Citraconic Anhydride as Precursors for CD‐Ring Fragments of Paclitaxel and Its Analogues
Author(s) -
Beusker Patrick H.,
M. Aben René W.,
Seerden JeanPaul G.,
Smits Jan M. M.,
Scheeren Hans W.
Publication year - 1998
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/(sici)1099-0690(199811)1998:11<2483::aid-ejoc2483>3.0.co;2-m
Subject(s) - chemistry , regioselectivity , furan , ring (chemistry) , ether cleavage , structural isomer , ether , cleavage (geology) , organic chemistry , bicyclic molecule , stereochemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
The high‐pressure promoted Diels–Alder reactions between several furans and citraconic anhydride have been studied and the cycloadducts obtained have been explored in new straightforward routes to the CD‐ring fragment of paclitaxel. The reaction between furan and citraconic anhydride afforded the exo cycloadduct diastereoselectively, whereas a variety of 2‐substituted furans afforded approximate 1:1 mixtures of exo regioisomers. Separation of both regioisomers was accomplished after either diastereoselective esterification or regioselective reduction of the anhydride function. Ether cleavage of the bicyclic compounds by either high‐pressure promoted ether cleavage or Boord elimination afforded several potential CD‐ring precursors which can be used in the total synthesis of paclitaxel analogues.