C O M M U N I C A T I O N S
Table 1. Development of Stereo- and Chemoselective Radical
Cyclization
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Acknowledgment. This work was supported financially by
SORST, Japan Science and Technology Agency (JST), and a Grant-
in-Aid for Scientific Research (S) from the Japan Society for the
Promotion of Science (JSPS). A fellowship to K.M. from JSPS is
gratefully acknowledged. We thank Professors Michio Murata
(Osaka University) and Masayuki Satake (University of North
Carolina) for providing NMR spectra of ciguatoxins.
(26) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118,
100.
(27) NAP is known to be oxidatively removable similarly to p-methoxybenzyl,
but is more acid-stable. For the development of our protective group
strategy, see ref 8b. For NAP ether references, see: (a) Gaunt, M. J.; Yu,
J.; Spencer, J. B. J. Org. Chem. 1998, 63, 4172. (b) Wright, J. A.; Yu, J.;
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(28) A preliminary toxicity study of the synthetic ciguatoxins was carried out
in mice. Acute toxicity on median lethal dose (LD50, intraperitoneal
injection) of 1 and 2 was determined to be 1.64 and 0.31 µg/kg,
respectively.
Supporting Information Available: Experimental procedures and
spectroscopic data for synthetic compounds (PDF). This material is
References
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