메뉴 건너뛰기




Volumn 8, Issue 15, 2006, Pages 3315-3318

Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; CLAVOSOLIDE A; MACROLIDE;

EID: 33746898578     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0611752     Document Type: Article
Times cited : (75)

References (36)
  • 13
    • 18744380352 scopus 로고    scopus 로고
    • (-)-Kendomycin: Smith, A. B., III; Mesaros, E. F.; Meyer, E. A. J. Am. Chem. Soc. 2005, 127, 6948.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 6948
  • 15
    • 33746895428 scopus 로고    scopus 로고
    • Concurrent with our efforts, Willis et al. also achieved the total synthesis of (-)-clavosolide A; see: Barry, C. S.; Elsworth, J. D.; Sedan, T. P.; Bushby, N.; Harding, R. J.; Alder, W. R.; Willis, L. C. Org. Lett. 2006, 8, 3319. We thank Professor Willis for helpful discussion during the course of this synthetic venture.
    • (2006) Org. Lett. , vol.8 , pp. 3319
    • Barry, C.S.1    Elsworth, J.D.2    Sedan, T.P.3    Bushby, N.4    Harding, R.J.5    Alder, W.R.6    Willis, L.C.7
  • 20
    • 0038275090 scopus 로고    scopus 로고
    • Anti-cyclopropanation of the TIPS-protected allylic alcohol led to a mixture (9:1) favoring the undesired syn-cyclopropylcarbinol (see: Charette, A. B.; Lacasse, M.-C. Org. Lett. 2002, 20, 3351)
    • (2002) Org. Lett. , vol.20 , pp. 3351
    • Charette, A.B.1    Lacasse, M.-C.2
  • 22
    • 33746916658 scopus 로고    scopus 로고
    • note
    • The order of addition (betaine formation) and temperature (-45 °C in toluene) in the Mitsunobu reaction proved to be critical to achieve high stereoselectivity.
  • 24
    • 33746874688 scopus 로고    scopus 로고
    • note
    • Enol acetal 14 was prepared in seven steps and 58% overall yield by a similar sequence as shown in Scheme 5 (excluding the Mitsunobu inversion).
  • 30
  • 35
    • 33746913752 scopus 로고    scopus 로고
    • note
    • See the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.