Download Carbohydrates - Tools for Stereoselective Synthesis by Mike Martin Kwabena Boysen PDF

By Mike Martin Kwabena Boysen

Remaining a niche within the literature, this entire publication provides such carbohydrate instruments as chiral auxiliaries, reagents, advanced ligands and organocatalysts, including information in their coaching, in addition to their winning software in stereoselective synthesis. It covers the synthesis of carbohydrate instruments, and discusses examples for a large variety of other reactions in comparison to these bought with the simplest traditional methods.
An quintessential resource for each natural chemist.

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2004) Synthesis, 2153–2164. , and Kunz, H. (1997) J. Org. , 62, 967–975. , and Sager, W. , 30, 4109–4110. , and Kunz, H. (2004) Curr. Org. , 8, 1739–1761. -J. (1991) Tetrahedron: Asymmetry, 2, 879–882. , and Tadano, K. (1999) Org.

Pumiliotoxin C, a representative of the cis-annulated decahydroquinoline alkaloids, was isolated from a glandular secretion of a South American frog of the genus Dendrobates. Some trans-annulated decahydroquinoline alkaloids are also known. The Kunz group completed the total synthesis of trans-annulated 4a-epi-pumiliotoxin C (74) from 70: Oxidative cleavage of the vinyl group in the side chain in 70, followed by base-mediated intramolecular aldol condensation of the resulting aldehyde, produced octahydroquinoline derivative 71.

3 the resulting chloride 16 eventually provided the auxiliary 17. Crotonylation of 17 provided the 3-O-crotonyl ester 18. The 1,4-additions of various organocuprates, prepared by mixing alkyl Grignard reagents and CuBr·Me2S, to 18 provided the 1,4-adducts 19 in moderate to high yield with approximately 90% de for R1 = Ph, vinyl, allyl, heptyl, Et, and i-Pr. The Hon group also explored the 1,4-additions of similar organocuprates to the corresponding 3-O-cinnamoyl derivative. In these cases, the diastereoselectivity was in general less practical.

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