Total synthesis of the putative structure of the novel triquinane natural product isocapnellenone

Tetrahedron Letters

Volumn 43, Issue 46, 2002, Pages 8301-8305

  Mehta, Goverdhan ^a   Krishna Murthy, A Sai ^a   Umarye, Jayant D ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ISOCAPNELL 9 EN 8 ONE; SESQUITERPENE DERIVATIVE; TRIQUINANE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG SYNTHESIS; HYDROGENATION; SPECTROMETRY; STEREOCHEMISTRY;

EID: 0037064398     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01978-0     Document Type: Article

References (25)

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5. For some of the recent accomplishments in the area of linear triquinane natural product syntheses, see: (a) Geng, F.; Liu, J.; Paquette, L. A. Org. Lett. 2002, 4, 71; (b) Mukai, C.; Kobayashi, M.; Kim, I. J.; Hanaoka, M. Tetrahedron 2002, 58, 5225; (c) Shindo, M.; Sato, Y.; Shishido, K. Tetrahedron Lett. 2002, 43, 5039; (d) Harrowven, D. C.; Lucas, M. C.; Howes, P. D. Tetrahedron 2001, 57, 9157; (e) Singh, V.; Alam, S. Q. Chem. Commun. 1999, 2519; (f) Singh, V.; Vedantham, P.; Sahu, P. K. Tetrahedron Lett. 2002, 43, 519.
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22. o) and 0.078 for all 3850 data. GOF (S)=1.094, restrained GOF=1.094 for all data. Structure was solved by direct methods (SIR-92). Refinement was by full-matrix least-squares using SHELXL-97. An ORTEP diagram with 50% ellipsoidal probability of compound (i) is shown in Fig. 1 .
23. o) and 0.1174 for all 4169 data. GOF (S)=1.077, restrained GOF=1.077 for all data. Structure was solved by direct methods (SIR-92). Refinement was by full-matrix least-squares using SHELXL-97. An ORTEP diagram with 50% ellipsoidal probability of compound 22 is shown in Fig. 2 .
24. After the acceptance of this paper we have been informed by Professor Romo de Vivar that the isocapnellane structures 7 and 8 assigned by them to the natural products from two Buddleia species were in error and have been shown to be identical with the well-known sesquiterpenoids (+)-cyclocolorenone and 1-hydroxycyclocolorenone, respectively (see corrigendum Phytochemistry 1996, 42, 1709).