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Alkene–Arene meta Photocycloadditions with a Four‐Carbon‐Atom Tether: Efficient Approach toward the Polycyclic Ring Systems of Aphidicolin and Stemodinone
Author(s) -
Boyd Joseph W.,
Greaves Nicola,
Kettle Jason,
Russell Andrew T.,
Steed Jonathan W.
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200461661
Subject(s) - ring (chemistry) , intramolecular force , aphidicolin , chemistry , alkene , substrate (aquarium) , allene , carbon fibers , carbon atom , cycloaddition , atom (system on chip) , stereochemistry , photochemistry , organic chemistry , materials science , composite number , computer science , embedded system , composite material , dna polymerase , catalysis , oceanography , geology , enzyme
At the end of its tether! The fusion of a six‐membered ring onto the four‐carbon‐atom tether of substrate 1 provides an efficient approach toward the polycyclic ring systems of the natural products aphidicolin and stemodinone. The reaction represents a unique example of a preference for product formation from an endo exciplex in an intramolecular system ( exo : endo 2 : 3 =1.0:1.2).