the chemical synthesis of tetrodoxin an ongoing questtetrodoxin化学合成的一个持续的追求.pdfVIP

Mar. Drugs 2011, 9, 2046-2074; doi:10.3390/md9102046 OPEN ACCESS Marine Drugs ISSN 1660-3397 /journal/marinedrugs Review The Chemical Synthesis of Tetrodoxin: An Ongoing Quest Jaclyn Chau and Marco A. Ciufolini * Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada; E-Mail: jchau@chem.ubc.ca * Author to whom correspondence should be addressed; E-Mail: ciufi@chem.ubc.ca; Tel.: +1-604-822-2419; Fax: +1-604-822-8710. Received: 9 September 2011; in revised form: 29 September 2011 / Accepted: 11 October 2011 / Published: 20 October 2011 Abstract: This contribution reviews all the synthetic work on tetrodotoxin that has appeared in the literature through June 2011. Keywords: tetrodotoxin; synthesis; nitrenes; hypervalent iodine compounds 1. Introduction This contribution reviews the literature on the synthesis of tetrodotoxin (TTX, 1, Figure 1), through the first half of 2011 [1]. This substance, the neurotoxic principle of the formidable Tetraodon fish (puffer fish, fugu), is one of the classical targets in synthetic organic chemistry. Its delightfully intricate architecture captured the imagination of the synthetic community as soon after its structure was determined independently, but nearly simultaneously, by Woodward [2], Goto [3], Tsuda [4], and respective collaborators, in the mid-1960s. Efforts to conquer TTX reached a climax in 1972, when Kishi and coworkers announced their history-making first synthesis of 1. Figure 1. Chemical structure of tetrodoto