A total synthesis of the styryllactone (+)-goniodiol from naphthalene.

No Thumbnail Available
File version
Author(s)
Banwell, MG
Coster, MJ
Edwards, AJ
Karunaratne, OP
Smith, JA
Welling, LL
Willis, AC
Griffith University Author(s)
Primary Supervisor
Other Supervisors
Editor(s)
Date
2003
Size
File type(s)
Location
License
Abstract

The cytotoxic natural product (+)-goniodiol was prepd. in twelve steps from enantiomerically pure cis-dihydrocatechol, which is readily obtained by microbial oxidn. of naphthalene. Elaboration of the cis-dihydrocatechol involves an initial oxidative cleavage to dialdehyde followed by redn. to give a diol. Conversion of the diol into an acetal required, inter alia, selective oxidn. of the benzylic alc. moiety followed by a metal-catalyzed decarbonylation of the resulting aldehyde. Allylation of I with allyltributylstannane in the presence of lithium perchlorate gave a ca. 2.7:1 mixt. of alcs., each of which was converted into the corresponding acrylate under std. conditions. Subjection of these ester derivs. to a ring-closing metathesis (RCM) reaction with Grubbs' first-generation catalyst gave the anticipated lactone II and its diastereomer. Acid-catalyzed removal of the acetonide protecting group within II then afforded (+)-goniodiol, while analogous deprotection of the congener afforded 6-epi-(+)-goniodiol.

Journal Title

Australian Journal of Chemistry

Conference Title
Book Title
Edition
Volume

56

Issue

6

Thesis Type
Degree Program
School
Publisher link
Patent number
Funder(s)
Grant identifier(s)
Rights Statement
Rights Statement
Item Access Status
Note
Access the data
Related item(s)
Subject

Chemical sciences

Persistent link to this record
Citation
Collections