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Volumn 12, Issue 7, 2010, Pages 1428-1431

Ga(IIl)-catalyzed cycloisomerization approach to (±)-icetexone and (±)-epi-icetexone

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; GADOLINIUM; ICETEXONE;

EID: 77950240527     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol902959v     Document Type: Article
Times cited : (38)

References (21)
  • 2
    • 0029105110 scopus 로고
    • For a review on abietane diterpenoids, see: (a) Ucar, G.; Fengel, D. Phytochemistry 1995 38, 877-880.
    • (1995) Phytochemistry , vol.38 , pp. 877-880
    • Ucar, G.1    Fengel, D.2
  • 6
    • 0342713529 scopus 로고
    • The structural assignments of icetexone and epi-icetexone were recently shown to be reversed (see ref 6). For isolation of icetexone and epi-icetexone, see: (a)
    • The structural assignments of icetexone and epi-icetexone were recently shown to be reversed (see ref 6). For isolation of icetexone and epi-icetexone, see: (a) Watson, W. H.; Taira, Z. Tetrahedron Lett. 1976 29, 2501-2502.
    • (1976) Tetrahedron Lett. , vol.29 , pp. 2501-2502
    • Watson, W.H.1    Taira, Z.2
  • 8
    • 33646873718 scopus 로고    scopus 로고
    • This paper reports studies on epi-icetexone. However, on the basis of the structural reassignments by Majetich (ref 6), the biological studies were conducted on icetexone.
    • Sanchez, A. M.; Jimenez-Ortiz, V.; Tonn, C. E.; Garcia, E. E.; Nieto, M.; Burgos, M. H.; Sosa, M. A. Acta Trop. 2006 98, 118-124. This paper reports studies on epi-icetexone. However, on the basis of the structural reassignments by Majetich (ref 6), the biological studies were conducted on icetexone.
    • (2006) Acta Trop. , vol.98 , pp. 118-124
    • Sanchez, A.M.1    Jimenez-Ortiz, V.2    Tonn, C.E.3    Garcia, E.E.4    Nieto, M.5    Burgos, M.H.6    Sosa, M.A.7
  • 10
    • 0028086375 scopus 로고
    • Cyclialkylation reactions for the synthesis of icetexane diterpenoids were pioneered by Majetich.
    • Cyclialkylation reactions for the synthesis of icetexane diterpenoids were pioneered by Majetich. For an early example, see: Majetich, G.; Zhang, Y. J. Am. Chem. Soc. 1994 116, 4979-4980.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 4979-4980
    • Majetich, G.1    Zhang, Y.2
  • 11
    • 84914202563 scopus 로고    scopus 로고
    • In preliminary studies conducted in these laboratories, fragmentation of the seven-membered ring was observed upon generation of the presumed alkoxy-radical intermediate. This is consistent with observations made by Majetich and co-workers, University of Georgia, Athens, GA
    • In preliminary studies conducted in these laboratories, fragmentation of the seven-membered ring was observed upon generation of the presumed alkoxy-radical intermediate. This is consistent with observations made by Majetich and co-workers, see: Li, Y. Ph.D. Dissertation, University of Georgia, Athens, GA, 2006 and ref 6.
    • (2006) Dissertation
    • Li, Y.1
  • 12
    • 84914202563 scopus 로고    scopus 로고
    • The synthesis of 22 reported herein was adapted from an earlier synthesis in our laboratories, University of California, Berkeley, CA
    • The synthesis of 22 reported herein was adapted from an earlier synthesis in our laboratories, see: Simmons, E. M. Ph.D. Dissertation, University of California, Berkeley, CA, 2009.
    • (2009) Dissertation
    • Simmons, E.M.1
  • 18
    • 77950247361 scopus 로고    scopus 로고
    • On the basis of the observed ratio of 7a to 7b, this trapping step likely proceeds with poor diastereocontrol.
    • On the basis of the observed ratio of 7a to 7b, this trapping step likely proceeds with poor diastereocontrol.
  • 20
    • 77950261207 scopus 로고    scopus 로고
    • The relative stereochemistry for 32 at C-5, which is inconsequential, was not established.
    • The relative stereochemistry for 32 at C-5, which is inconsequential, was not established.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.