Enantioselective Synthesis of Altohyrtin C (Spongistatin 2): Synthesis of the EF-Bis(pyran) Subunit

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 24, 1997, Pages 2741-2744

  Evans, David A ^a   Trotter, B Wesley ^a   Côté, Bernard ^a   Coleman, Paul J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

Altohyrtin; Antitumor agents; Natural products; Spongistatin; Total synthesis

Indexed keywords

EID: 0032491812     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199727411     Document Type: Article

References (34)

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5. 29 (E ring) segments has been assigned differently in the altohyrtin, spongistatin, and cinachyrolide series: a) M. Kobayashi, S. Aoki, K. Gato, I. Kitagawa, Chem. Phar. Bull. 1996, 44, 2142-2149; b) R. Bai, G. F. Taylor, Z. A. Cichacz, C. L. Herald, J. A. Kepler, G. R. Pettit, E. Hamel, Biochemistry 1995, 34, 9714-9721; c) N. Fusetani, K. Shinoda, S. Matsunaga, J. Am. Chem. Soc. 1993, 115, 3977-3981.
6. 29 (E ring) segments has been assigned differently in the altohyrtin, spongistatin, and cinachyrolide series: a) M. Kobayashi, S. Aoki, K. Gato, I. Kitagawa, Chem. Phar. Bull. 1996, 44, 2142-2149; b) R. Bai, G. F. Taylor, Z. A. Cichacz, C. L. Herald, J. A. Kepler, G. R. Pettit, E. Hamel, Biochemistry 1995, 34, 9714-9721; c) N. Fusetani, K. Shinoda, S. Matsunaga, J. Am. Chem. Soc. 1993, 115, 3977-3981.
7. Abbreviations: dr=diastereomer ratio; TBS=tert-butyldimethylsilyl: TES=triethylsilyl; TMS=trimethylsilyl; DIBALH=diisobutylaluminum hydride; Tr=trityl=triphenylmethyl; Tf=trifluoromethanesulfonyl; Bn= benzyl; PPTS=pyridinium p-toluenesulfonate; CSA=camphorsulfonic acid; LDBB=di-tert-butylbiphenyllithium; DMAP=4-dimethylaminopyridine; 9-BBN=9-borabicyclo[3.3.1]nonane; m-CPBA=m-chloroperbenzoic acid; LDA=lithium diisopropylamide HMPA=hexamethylphosphoric triamide.
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31. The authors wish to thank Kevin R. Campos for performing the X-ray analysis of 27.
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34. D. A. Evans, B. W. Trotter, B. Côté, P. J. Coleman, L. C. Dias, and A. N. Tyler, Angew. Chem. 1997, 109, 2957-2961; Angew. Chem. Int. Ed. Engl. 1997, 36, 2744-2747.