Short and efficient synthesis of cryptophycin unit A

Eissler S, Nahrwold M, Neumann B, Stammler H-G, Sewald N (2007)
ORGANIC LETTERS 9(5): 817-819.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
Two short synthetic approaches toward cryptophycin unit A comprise a catalytic asymmetric dihydroxylation as the sole source of chirality, while all further stereogenic centers are introduced under substrate control. The key step of the first route is a vinylogous Mukaiyama aldol addition, which introduces the alpha,beta-unsaturated ester moiety with defined configuration at the delta-carbon atom. Likewise, allylation with allyltributylstannane diastereoselectively gives the homoallylic alcohol that can be converted by a metathesis reaction to a unit A precursor.
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ORGANIC LETTERS
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9
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Eissler S, Nahrwold M, Neumann B, Stammler H-G, Sewald N. Short and efficient synthesis of cryptophycin unit A. ORGANIC LETTERS. 2007;9(5):817-819.
Eissler, S., Nahrwold, M., Neumann, B., Stammler, H. - G., & Sewald, N. (2007). Short and efficient synthesis of cryptophycin unit A. ORGANIC LETTERS, 9(5), 817-819. doi:10.1021/ol063032l
Eissler, S., Nahrwold, M., Neumann, B., Stammler, H. - G., and Sewald, N. (2007). Short and efficient synthesis of cryptophycin unit A. ORGANIC LETTERS 9, 817-819.
Eissler, S., et al., 2007. Short and efficient synthesis of cryptophycin unit A. ORGANIC LETTERS, 9(5), p 817-819.
S. Eissler, et al., “Short and efficient synthesis of cryptophycin unit A”, ORGANIC LETTERS, vol. 9, 2007, pp. 817-819.
Eissler, S., Nahrwold, M., Neumann, B., Stammler, H.-G., Sewald, N.: Short and efficient synthesis of cryptophycin unit A. ORGANIC LETTERS. 9, 817-819 (2007).
Eissler, Stefan, Nahrwold, Markus, Neumann, Beate, Stammler, Hans-Georg, and Sewald, Norbert. “Short and efficient synthesis of cryptophycin unit A”. ORGANIC LETTERS 9.5 (2007): 817-819.

5 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

The vinylogous Mukaiyama aldol reaction (VMAR) in natural product synthesis.
Kalesse M, Cordes M, Symkenberg G, Lu HH., Nat Prod Rep 31(4), 2014
PMID: 24595879
Recent approaches for the synthesis of modified cryptophycins.
Weiss C, Sammet B, Sewald N., Nat Prod Rep 30(7), 2013
PMID: 23732943
Total synthesis and biological evaluation of fluorinated cryptophycins.
Weiß C, Bogner T, Sammet B, Sewald N., Beilstein J Org Chem 8(), 2012
PMID: 23209540
Efficient synthesis of cryptophycin-52 and novel para-alkoxymethyl unit A analogues.
Eissler S, Bogner T, Nahrwold M, Sewald N., Chemistry 15(42), 2009
PMID: 19760734

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