Acyclic Stereocontrol Induced by Allylic Alkoxy Groups. Synthetic Applications of Stereoselective Dihydroxylation in Natural Product Synthesis

Chemical Reviews

Volumn 95, Issue 6, 1995, Pages 1761-1795

  Cha, Jin Kun ^a   Kim, No Soo ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 11944249437     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr00038a003     Document Type: Article

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276. Subsequently Pattenden extenid Vleggaar's postulate to the 2,6-dioxabieyclo[3.2.1] system of aurovertins (141), where a cascade of cyclizations of a triepoxide was considered: Forbes, J. E.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1991, 1959-1966.
277. An epoxide-mediated rearrangement involving a triepoxide was previously advanced by Vleggaar to account for the formation of the 2,8-dioxabicyelo[3.3.0]octane moiety of asteltoxin (148), a structurally unique member of this citreoviridin family: (a) de Jesus, A. E.; Steyn, P. S.; Vleggaar, R. J. Chem. Soc., Chem. Commun. 1985, 1633-1635.
278. Recently we have successfully accomplished a formal synthesis of 148 in parallel to Vleggaar's biosynthetic postulate: Raman, J. V.; Lee, H. K.; Vleggaar, R.; Cha, J. K. Tetrahedron Lett. 1995, 36, 3095-3098.
279. In this connection, the coisolation of citreodiol, along with 139, 140, and 142, from Penicillium citreoviride, might be significant.1535 It should be added that citreomontanin, a C18-polyene a-pyrone, was also isolated from Penicillium sp., but failed to be incorporated into 139: Rebuffat, S.; Davoust, D.; Molho, L.; Molho, D. Phytochemistry 1980, 19, 427-431. Synthesis: (a) Patel, P.; Pattenden, G. Tetrahedron Lett. 1985, 26, 4789-4792.
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286. (R)-Antipodes are shown for uniformity, although 168a-c were prepared in the S-configuration starting from readily available ethyl
287. (-)-lactate.
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317. Reference 82.
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328. Fleming, I.; Lawrence, N. J. Tetrahedron Lett. 1988, 29, 2077-2080.
329. Compare: Directed, rhodium
330. or iridium
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340. In general, the syn isomer 215 is slightly favored for allylic alcohols and, to a greater extent, the anti isomer 214 for allylic ethers. Stereoselective nitrile oxide cycloaddition reactions have been reviewed: (a) Annunziata, R.; Cinquini, M.; Cozzi, F.; Raimondi, L. Gazz. Chim. Ital. 1989,119, 253-269.
341. Easton, C. J.; Hughes, C. M. M.; Savage, G. P.; Simpson, G. W. Adv. Heterocycl. Chem. 1994, 60, 261-327.
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345. DeShong, P.; Leginus, J. M. J. Am. Chem. Soc. 1983,105,1686-1688.
346. An interesting comparison was made between osmylation and nitrile oxide cycloaddition of the identical allylic ether substrate (Table 5, entries 1 and 2). Both reactions were found to proceed with the same level (4:1) of diastereoselectivity: ref 31.
347. Chamberlin, A. R.; Mulholland, R. L., Jr. Tetrahedron 1984, 40,2297-2302.
348. Reference 77. Compare
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350. For an excellent review of earlier work, see: Partlett, P. A. In Asymmetric Synthesis’, Morrison, J. D., Ed.; Academic Press: Orlando, FL, 1984; Vol. 3, pp 411-454.
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