Clavulactone (1) is an unusual dolabellane diterpene isolated from the Pacific soft coral Clavularia viridis. Its unprecedented tricyclic structure and antitumor activity motivate the studies described in this proposal. Daunting challenges posed by 1 include the remote stereocenter at C8, the quaternary carbon center at C1, and the potentially strained eleven-membered medium ring. Our synthesis plan incorporates macrocyclic stereocontrol, catalytic asymmetric conjugate addition of an alkyl metal reagent, and a fascinating intramolecular hetero Diels-Alder reaction. ? ?

Agency
National Institute of Health (NIH)
Institute
National Cancer Institute (NCI)
Type
Postdoctoral Individual National Research Service Award (F32)
Project #
5F32CA101531-02
Application #
6867389
Study Section
Special Emphasis Panel (ZRG1-F04 (20))
Program Officer
Lohrey, Nancy
Project Start
2003-05-01
Project End
2005-06-30
Budget Start
2004-07-01
Budget End
2005-06-30
Support Year
2
Fiscal Year
2004
Total Cost
$42,976
Indirect Cost
Name
Harvard University
Department
Chemistry
Type
Schools of Arts and Sciences
DUNS #
082359691
City
Cambridge
State
MA
Country
United States
Zip Code
02138