By Stephen P. Hopkin
This accomplished paintings is the 1st single-volume publication of the twentieth century to study the biology of this significant team of bugs, together with a whole checklist of Collembola genera including greater than 2,500 references in addition to the discussions of springtail habit, body structure and evolution.
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NaN3, DMF (79%) 2. ACOH (68%) O"3 Ar = p-OHC6H4 y,^Y—-Ar [ J CO2Me O ^^ / 134 Ar = p-OprenylC6H4 Me" LiAIH4 2. HCO2Ac 3. LiAIH4 (58%) TFAA, Et3N, POCF, CH2OH o 136 135 K2CO3, MeOH/H2O (60% from 135) f 129 (+)-TAN1251C(4) Scheme 40. Snider's synthesis of (+)-TAN125lC The synthesis starts from the N-Boc-tyrosine methyl ester, which was Obenzylated, since the prenyl ether required in the target compound is not compatible with the conditions required for the preparation of the hydoxylamine or the hydrogenation of the isoxazolidine intermediate (Scheme 40).
LiBH 4 , THF 2. HCI, AcOH, H2O (97%) N(Boc)Me 3. Boc2O, Et3N (95%) 4. Dess Martin 2. TFA, CH 2 CI 2 6 (PG = Boc) OMe OMe NHMe 25 (36%) OMe NHMe 26 (16%) 27 (5%) Scheme 10. Preparation of ketoaldehyde 6 and its aldol reaction UBH4 followed by an acid hydrolysis gave a deprotected keto alcohol, in which the secondary amine was again protected with BOC2O. Finally, the aldehyde intermediate 6 was obtained using the Dess Martin reagent. The aldol reaction of 6 proceeded analogously to that of the model ketoaldehyde 12, although in lower yield.
Ac2O, Py (41 %) lyie TPAP, NMO first generation <^N ^ (77%) ' 1. Ac2O, Py 2. L- Selectride NaOMe, 90%aq MeOH ~ UMU Y (44%) O 6 (PG=Ts) second generation 1. LiAIH4 (53 %) 59 2. (BnO)2PO2H, (C6H4CI)3P, DIAD, then Et3N 3. HCI •l< Cbz (29 %) OPO(OBn)2 Scheme 22. Ciufolini's synthesis of (-)-FR901483 58 (94%) 25 This somewhat surprising stereochemical result is attributable to the greater reactivity, and hence the lower selectivity, of LAH relative to other reducing agents. Working with alcohol 59 and its epimer at C(9), the Mitsunobu process leads to phosphate 58, as the major product, after conversion of the resulting extremely polar compounds to their iV-Cbz derivatives.
Biology of Springtails by Stephen P. Hopkin
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