Samarium(II) induced asymmetric reductive cyclizations: The total synthesis of (-)-C{sub 10} desmethyl arteannuin B
Conference
·
OSTI ID:250142
- Univ. of California, Santa Barbara, CA (United States)
Arteannuin B is a member of the qinghaosu family, a novel class of sesquiterpenes that exhibit powerful antimalarial activity even against chloroquinine resistant strains. It is readily convertible to qinghaosu in several high yielding steps and has potential antitumor activity. Several approaches to the construction of the cis-decalin backbone have involved the use of electrochemical and metal promoted reductions as well as alkylations. We report a short convenient total synthesis of (-)-C{sub 10} desmethyl arteannuin B utilizing an asymmetric reductive cyclization with samarium (II) iodide which selectively forms the cis-decalin ring structure while setting the trans relationship between the subunits of the {gamma}-hydroxy ester.
- OSTI ID:
- 250142
- Report Number(s):
- CONF-9508100--
- Country of Publication:
- United States
- Language:
- English
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