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Synlett 2011(5): 651-654  
DOI: 10.1055/s-0030-1259546
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Bromocyclization of Alkynyl Guanidine: A New Approach to the Synthesis of Cyclic Guanidines of Saxitoxin

Yusuke Sawayama, Toshio Nishikawa*
Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan
Fax: +81(52)7894111; e-Mail: nisikawa@agr.nagoya-u.ac.jp;
Further Information

Publication History

Received 21 December 2010
Publication Date:
11 February 2011 (online)

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Abstract

Bromocyclization of propargyl and homopropargyl guanidines possessing homopropargyl alcohol provides five- and six-membered cyclic guanidines with spiro-hemiaminal, respectively, a candidate of precursors for saxitoxin.

Key words

saxitoxin - cyclic guanidine - alkynyl guanidine - bromocyclization - spiro-hemiaminal

    References and Notes

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17

The structure of 14 was supported by extensive NMR analysis of the di-Boc analogue of 14 (as a single product) prepared from 6 with di-Boc-methylisothiourea in a similar manner. See Supporting Information.