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Total Syntheses of Naturally Occurring Molecules Possessing 1,7‐Dioxaspiro[4.4]nonane Skeletons
Author(s) -
C. Wong Henry N.
Publication year - 1999
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(199908)1999:8<1757::aid-ejoc1757>3.0.co;2-u
Subject(s) - nonane , chemistry , regioselectivity , intramolecular force , stereoselectivity , stereochemistry , molecule , combinatorial chemistry , organic chemistry , catalysis
The syntheses of several naturally occurring molecules, namely prehispanolone, sphydrofuran, secosyrins, and syringolides are reviewed. Interestingly, these compounds are all structurally related, possessing a 1,7‐dioxaspiro[4.4]nonane framework. The pivotal step in these synthetic endeavors involves the peracid oxidation of substituted 2‐trimethylsilylfurans to but‐2‐en‐4‐olides. A subsequent intramolecular Michael addition procedure was also essential in the construction of the spiro skeleton. Two significant issues concerning regioselectivity and stereoselectivity are also addressed.