Synthetic studies on Ecteinascidin-743: synthesis of building blocks through Sharpless asymmetric dihydroxylation and aza-Michael reactions |
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Authors: | S. Chandrasekhar N. Ramakrishna Reddy Y. Srinivasa Rao |
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Affiliation: | Indian Institute of Chemical Technology, Organic Division-I, Natural Products Laboratory, Tarnaka, Hyderabad 500 007, Andhra Pradesh, India |
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Abstract: | A practical and an efficient synthesis of three building blocks of tetrahydroisoquinoline alkaloid Ecteinascidin-743 was accomplished, starting from readily available piperonal, 2-methyl anisole, and veratraldehyde. A combination of Vilsmeier-Haack reaction and Sharpless asymmetric dihydroxylation was employed for the synthesis of building blocks A and B whereas a Heck reaction in PEG-2000 and aza-Michael reactions were employed for the synthesis of building block C. |
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Keywords: | Ecteinascidin-743 Tetrahydroisoquinolines Heck reaction Aza-Michael reaction Baeyer-Villiger reaction |
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