- Total synthesis of the ansamycin antibiotic (+)-thiazinotrienomycin E
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The first total synthesis of (+)-thiazinotrienomycin E (1), member of a novel class of cytotoxic ansamycin antibiotics, has been achieved. Key features of the synthetic strategy include (a) the efficient construction of sulfone 7 incorporating TBS protection of the aniline, (b) an improved synthesis of allyl chloride (-)-6, the advanced intermediate employed in our trienomycins A and F total syntheses, (c) application of the Kocienski modified Julia protocol to elaborate the E,E,E-triene subunit in a stereo- controlled fashion, (d) an efficient union of sulfone 7 with advanced iodide 62, and (e) Mukaiyama macrolactamization to access the thiazinotrienomycin macrocyclic ring.
- Smith III, Amos B.,Wan, Zehong
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p. 3738 - 3753
(2007/10/03)
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- Total synthesis of (+)-thiazinotrienomycin E
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(equation presented) The first total synthesis of (+)-thiazinotrienomycin E (1), member of a novel class of cytotoxic ansamycin antibiotics, has been achieved. The synthesis features a highly efficient construction of the aromatic fragment 3 incorporating
- Smith III, Amos B.,Wan, Zehong
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p. 1491 - 1494
(2008/02/09)
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- A Complex Induced Proximity Effect in the Anionic Fries Rearrangement of o-Iodophenyl Benzoates: Synthesis of Dihydro-O-methylsterigmatocystin and Other Xanthones
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The success of an anionic Fries rearrangement, used to synthesise dihydro-O-methylsterigmatocystin and other xanthones, is dependent on the presence of a remote methoxyl substituent.
- Horne, Stephen,Rodrigo, Russell
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p. 4520 - 4522
(2007/10/02)
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