Cryptophycin-39 Unit A Precursor Synthesis by a Tandem Shi Epoxidation and Lactonization Reaction of trans-Styryl Acetic Acid

Sammet B, Radzey H, Neumann B, Stammler H-G, Sewald N (2009)
SYNLETT 2009(03): 417-420.

Journal Article | Published | English

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Abstract
Unit A of cryptophycins is a delta-hydroxy acid with two or four stereogenic centers. The first synthesis of the unit A building block of cryptophycin-39 is based on a catalytic asymmetric Shi epoxidation of trans-styryl acetic acid followed by an in situ lactonization. The scope of this reaction has been investigated with respect to various beta,gamma-unsaturated carboxylic acids as substrates for the asymmetric synthesis of 4-hydroxy-5-phenyl-tetrahydrofuran-2-ones under Shi conditions.
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Sammet B, Radzey H, Neumann B, Stammler H-G, Sewald N. Cryptophycin-39 Unit A Precursor Synthesis by a Tandem Shi Epoxidation and Lactonization Reaction of trans-Styryl Acetic Acid. SYNLETT. 2009;2009(03):417-420.
Sammet, B., Radzey, H., Neumann, B., Stammler, H. - G., & Sewald, N. (2009). Cryptophycin-39 Unit A Precursor Synthesis by a Tandem Shi Epoxidation and Lactonization Reaction of trans-Styryl Acetic Acid. SYNLETT, 2009(03), 417-420.
Sammet, B., Radzey, H., Neumann, B., Stammler, H. - G., and Sewald, N. (2009). Cryptophycin-39 Unit A Precursor Synthesis by a Tandem Shi Epoxidation and Lactonization Reaction of trans-Styryl Acetic Acid. SYNLETT 2009, 417-420.
Sammet, B., et al., 2009. Cryptophycin-39 Unit A Precursor Synthesis by a Tandem Shi Epoxidation and Lactonization Reaction of trans-Styryl Acetic Acid. SYNLETT, 2009(03), p 417-420.
B. Sammet, et al., “Cryptophycin-39 Unit A Precursor Synthesis by a Tandem Shi Epoxidation and Lactonization Reaction of trans-Styryl Acetic Acid”, SYNLETT, vol. 2009, 2009, pp. 417-420.
Sammet, B., Radzey, H., Neumann, B., Stammler, H.-G., Sewald, N.: Cryptophycin-39 Unit A Precursor Synthesis by a Tandem Shi Epoxidation and Lactonization Reaction of trans-Styryl Acetic Acid. SYNLETT. 2009, 417-420 (2009).
Sammet, Benedikt, Radzey, Hanna, Neumann, Beate, Stammler, Hans-Georg, and Sewald, Norbert. “Cryptophycin-39 Unit A Precursor Synthesis by a Tandem Shi Epoxidation and Lactonization Reaction of trans-Styryl Acetic Acid”. SYNLETT 2009.03 (2009): 417-420.
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