Download Synthesis of Marine Natural Products 1: Terpenoids by K.F. Albizati, V.A. Martin, M.R. Agharahimi, D.A. Stolze PDF

By K.F. Albizati, V.A. Martin, M.R. Agharahimi, D.A. Stolze

Volumes 5 and 6 of Bioorganic Marine Chemistry range from their predecessors in respects - they deal solely with hard work­ atory synthesis of marine average items and so they symbolize the trouble of a unmarried writer and his affiliates. the reason for those departures is instantly perceived. For a number of a long time natural synthesis has definitely been the main unbelievable department of natural chemistry. whereas the past due R.B. Woodward's dictum - natural compounds can suffer purely 4 uncomplicated reactions: they could achieve electrons; they could lose electrons; they are often reworked with acid or with base - continues to be actual, the wealth and diversity of accessible reagents with the intention to accomplish chemical modifications has reached stunning proportions. Little ask yourself then, that artificial technique has accomplished a excessive measure of predictability and overall synthesis of usual items has been effectively directed towards ever more difficult objectives. As for the second one element, that of unmarried authorship, a number of authorship may consistently have resulted in gaps and overlaps, hence making it tough to gather and determine fresh examine in a scientific and comprehens­ ive fashion.

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5 Pallescensin-l Pallescensin-l was first prepared as a mixture with pallescensin A in an enantiospecific, but nonstereospecific, synthesis by Matsumoto and has already been detailed (Scheme 36). Pailescensin 1 203 The second synthesis of pallescensin-l is that of Tius [76], outlined in Scheme 41. ' The synthesis begins with formation of the O-trimethylsilyl cyanohydrin 225 of aldehyde 224 (available from famesol). PDe oxidation of 225 in dry DMF affords diene butenolide 226. Treatment of 226 with tin(IV) chloride produces the cydized product 227 in 60% yield, along with 10% ofthe L\6,13-isomer and a trace ofthe L\5,6-isomer.

H2S04 218 50% Scheme 39. Oishi Synthesis of (+ )-Pallescensin A (+)-pallescensin A 204 .. : H 220 1\ NH2NH2 KOH triethylene glycol .. Q) QJ 0 3NHCI THF 98% 93% .. 221 I) LDAITHF .. 2)TMSCI 3) Allyl bromide + PhCH2NMe3 F 59% .. ~o 84% 222 223 PhH (H20 removal) 35% .. (+)-pallescensin A 204 optically active, but thought to have partially racemized via a planar intermediate Scheme 40. 5 Pallescensin-l Pallescensin-l was first prepared as a mixture with pallescensin A in an enantiospecific, but nonstereospecific, synthesis by Matsumoto and has already been detailed (Scheme 36).

Selective tosylation of the diol 158, allylic oxidation, and displacement of the tosyl group provides the cr-ketosulfone 159. Coupling of 159 with 3-furylmethyl bromide provides ketone 160, which is reduced with sodium borohydride to give the alcohol. Acetylation of the alcohol and reductive elimination of the p-acetoxysulfone provides pleraplysillin-1 (161) with the correct E,E-diene geometry. The metabolite is obtained in 9 steps and 24 % overall yield. Pleraplysillin-l 161 Stille [56] developed a very short and efficient synthesis of pleraplysillin-1 based on the palladium-catalyzed coupling of vinyl triflates with organostannanes (Scheme 28).

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