Norrisolide: total synthesis and related studies.
A stereoselective synthesis of (+)-norrisolide is presented. This natural product belongs to a family of marine spongiane diterpenes the structure of which is characterized by a fused gamma-lactone-gamma-lactol ring system attached to a bicyclic hydrophobic core. Our studies led to the development of a expedient synthesis of such gamma-lactone-gamma-lactol motifs based on ring expansion of a fused cyclopropyl ester. Highlights of the synthetic strategy toward norrisolide include the coupling of the two bicyclic systems by constructing a sterically demanding C9-C10 bond and the installation of the C19 oxygen at the last step of the synthesis via a Baeyer-Villiger oxidation.
Brady
Thomas P
TP
Department of Chemistry and Biochemistry, University of California at San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358, USA.
Kim
Sun Hee
SH
Wen
Ke
K
Kim
Charles
C
Theodorakis
Emmanuel A
EA
D000818:Animals; D004224:Diterpenes / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008974:Mollusca / Q000737:chemistry*; D010084:Oxidation-Reduction; D014961:X-Ray Diffraction
D004224:Diterpenes; C485194:norrisolide