Total synthesis of scytophycin C

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 452-453

  Paterson, Ian ^a   Watson, Christine ^a   Yeung, Kap Sun ^a   Wallace, Paul A ^a   Ward, Richard A ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; MACROLIDE; SCYTOPHYCIN C; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031025353     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962189w     Document Type: Article

References (27)

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2. (b) Moore, R. E.; Patterson, G. M. L.; Mynderse, J. S.; Barchi, J., Jr.; Norton, T. R.; Furusawa, E.; Furusawa, S. Pure Appl. Chem. 1986, 58, 263.
3. Carmeli, S.; Moore, R. E.; Patterson, G. M. L.; Yoshida, W. Y. Tetrahedron Lett. 1993, 34, 5571.
4. For scytophycins isolated from other species of Scytonema and Cylindrospermum musicola, see: (a) Carmeli, S.; Moore, R. E.; Patterson, G. M. L. J. Nat. Prod. 1990, 53, 1533. (b) Jung, J. H.; Moore, R. E.; Patterson, G. M. L. Phytochemistry 1991, 30, 3615.
5. For scytophycins isolated from other species of Scytonema and Cylindrospermum musicola, see: (a) Carmeli, S.; Moore, R. E.; Patterson, G. M. L. J. Nat. Prod. 1990, 53, 1533. (b) Jung, J. H.; Moore, R. E.; Patterson, G. M. L. Phytochemistry 1991, 30, 3615.
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13. The scytophycins are structurally related to the swinholides, a group of dimeric, 44-membered macrodiolides from Theonella swinhoei. Kitagawa, I.; Kobayashi, M.; Katori, T.; Yamashita, M.; Tanaka, J.; Doi, M.; Ishida, T. J. Am. Chem. Soc. 1990, 112, 3710.
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19. 27 in 9 assumes that Felkin-Anh selectivity is operating in the reduction.
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22. 27, completely failed to give any macrolides under the normal Yamaguchi conditions. This is due to hemiacetal formation with the 23-OH, which presumably sterically blocks the 21-OH from acylation.
23. Kigoshi, H.; Suenaga, K.; Mutou, T.; Ishigaki, T.; Atsumi, T.; Ishiwata, H.; Sakakura, A.; Ogawa, T.; Ojika, M.; Yamada, K. J. Org. Chem. 1996, 61, 5326.
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26. Paterson, I.; Cowden, C.; Watson, C. Synlett 1996, 209.
27. Unfortunately, an authentic sample of scytophycin C was not available from the Hawaii group (Dr. G. M. L. Patterson) for direct comparison.