By Robert H. Grubbs, Daniel J. O'Leary
The moment variation of the "go-to" reference during this box is totally up-to-date and lines greater than eighty% new content material, with emphasis on new advancements within the box, specifically in business functions. No different book
covers the subject in this kind of accomplished demeanour and in such excessive quality.
Edited by way of the Nobel laureate R. H. Grubbs and D. J. O´Leary, quantity 2 of the 3-volume paintings focusses on purposes in natural synthesis. With an inventory of members that reads like a "Who's-Who" of metathesis, this can be an
indispensable one-stop reference for chemists in academia and industry.
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Extra resources for Handbook of Metathesis, Volume 2: Applications in Organic Synthesis
37) . In addition to its important biological activity, garsubellin A has several challenging structural features, including a tricyclic core and two all-carbon quaternary stereocenters. Starting with the O-allyl substrate 218, a stereoselective Claisen rearrangement was utilized to build the congested quaternary center present in 219. The crucial B ring was formed by RCM to aﬀord the bicyclic product 220 in excellent yield. This product was then further subjected to various transformations to provide garsubellin A (221).
NCS, MeOH, rt 2. TBAF, H2O, THF, rt 62%, 3 steps from 100 p-TsOH 71% Et2O, rt Me HO 2. 19 Poitediol (102) Me H Isodactylol (104) Me H 105 Me Synthesis of poitediol, dactylol, iso-dactylol, and chlorinated analog. 20) . When allylic sulfoximine 106 was treated with n-BuLi, ClTi(OiPr)3 , and various aldehydes at −78 ∘ C, it aﬀorded the corresponding sulfoximine-substituted homoallylic alcohols 107a,b in 70–75% yield with ≥96% de. Silylation with TESCl gave sulfoximines 108a,b, and subsequent α-allylation provided E-sulfoximine-substituted trienes 109a,b as single isomers.
2 Me H Me Steps OHC O Me 3. HCl 70% , 3 steps Me Me 116 Me H 1. LDA, TMSCl HO 2. m-CPBA O Me Me 117 1. MeMgI 95% AcO 2. , AcCl 85% Me 3. PCC, 80% Me 118 G-II toluene HO Me Me H O Me Me Me 1. 2. DMP, 85% MgCl 90% Me HO Me 80 °C, 90% Me Me 19 119 Me Me 1. MsCl, Et3N Me O Me 2. 21 Carbocycles (Introduction) Me 121 120 Enantiospeciﬁc total synthesis of (−)-parvifoline. 22) . They synthesized the radical precursor 128 in 88% yield using a 10-membered RCM of diene 127. The synthesis of the RCM substrate began with a Mukaiyama–Keck aldol reaction of aldehyde 123 using silyl ether 124 to aﬀord the β-hydroxy ester 125 in 89% yield and 89% ee.
Handbook of Metathesis, Volume 2: Applications in Organic Synthesis by Robert H. Grubbs, Daniel J. O'Leary