Author
M. Nagamochi
Bio: M. Nagamochi is an academic researcher from Tohoku University. The author has contributed to research in topics: Total synthesis & Enantioselective synthesis. The author has an hindex of 9, co-authored 17 publications receiving 294 citations.
Papers
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TL;DR: A remarkable substituent effect by the tert-butyldimethylsiloxy group on the enantioselectivity of the tandem asymmetric epoxidation and enantiospecific ring expansion of 2-[2-cyclopropylideneethanol]-2-hydroxymethylcyclobutanone in high yield and high enantiomeric excess was observed.
Abstract: A remarkable substituent effect by the tert-butyldimethylsiloxy group on the enantioselectivity of the tandem asymmetric epoxidation and enantiospecific ring expansion of 2-[2-(tert-butyldimethylsiloxy)-4-methylphenyl]-2-cyclopropylideneethanol (18), affording (S)-(-)-2-[2-(tert-butyldimethylsiloxy)-4-methylphenyl]-2-hydroxymethylcyclobutanone (21) in high yield and high enantiomeric excess, was observed. This enabled us to accomplish a concise and highly enantioselective total synthesis of (-)-debromoaplysin (2) and (-)-aplysin (1), providing a new and general strategy for the enantioselective synthesis of biologically important substances having the dihydrobenzofuran framework
74 citations
TL;DR: In this article, a tandem Katsuli-Sharpless asymmetric epoxidation and enantiospecific ring expansion of 2-alkyl(or 2-aryl)-2-cyclopropylideneethanols (1a-i) afforded chiral 1-alky(or 1-aryl)1-(hydroxymethyl)cyclobutanones (3a)-i) in high yields and high enantiomeric excess.
Abstract: A tandem Katsuli-Sharpless asymmetric epoxidation and enantiospecific ring expansion of 2-alkyl(or 2-aryl)-2-cyclopropylideneethanols (1a-i) afforded chiral 1-alkyl(or 1-aryl)-1-(hydroxymethyl)cyclobutanones (3a-i) in high yields and high enantiomeric excess. These compounds are potentially valuable synthons for the enantioselective creation of the quaternary carbons. Hence, this enabled us to accomplish a concise and enantioselective total synthesis of both (+)- and (-)-α-cuparenones
71 citations
TL;DR: The first examples of asymmetric dihydroxylation (AD) of cyclopropylidene derivatives were reported in this article, followed by enantiospecific 1,2-rearrangement of the resulted diols to give the optically active cyclobutanones 15a∼d and 11, and also the first enantiocontrolled total synthesis of (-)-debromofiliformin (7a) and (-)-filiformin starting from 11 via the regioc-controlled cyclization of the phenolic allyl alcohol
37 citations
TL;DR: In this article, a novel and convenient route to the thermodynamically unstable ketone via the cyclopentanone 8 which was synthesised by palladium-mediated ring expansion of the chiral siloxyvinylcyclobutanes 9 and 10 has been developed.
Abstract: A novel and convenient route to the thermodynamically unstable ketone 11via the cyclopentanone 8 which was synthesised by palladium-mediated ring expansion of the chiral siloxyvinylcyclobutanes 9 and 10 has been developed. This leads to an enantioselective total synthesis of (+)- laurene 1.
27 citations
TL;DR: In this article, the regiocontrolled hydrogenation of the cyclohexadiene 6, synthesised from the chiral cyclobutanone 3 was effectively achieved with [1,4-bis(diphenylphosphino)butane]-1,5-cyclooctadiene)rhodium (1) tetrafluoroborate as catalyst to give the olefins 7 and 8 which were converted into (−)-α-bisabolol 1a and (+)-4-epi-α-isabolol 15via
24 citations
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TL;DR: This review covers the literature published in 2014 for marine natural products, with 1116 citations referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms.
4,649 citations
TL;DR: Transformation of Cyclobutane Derivatives inNatural Product Syntheses: A Review of the Transformations in Organic Syntheses.
Abstract: I. Introduction 1485II. Scope of This Review 1485III. Transformations of Cyclobutane Derivatives inOrganic Syntheses1486A. Ring-Opening Reactions 1486B. Ring-Contraction Reactions 1493C. Ring-Expansion Reactions 14951. Five-Membered Rings 14952. Six-Membered Rings 15093. Seven-Membered Rings 15174. Eight-Membered Rings 15215. Nine-Membered Rings 1523IV. Transformations of Cyclobutane Derivatives inNatural Product Syntheses1524A. Ring-Opening Reactions 1524B. Ring-Expansion Reactions 15261. Five-Membered Rings 15262. Six-Membered Rings 15293. Seven-Membered Rings 15324. Eight-Membered Rings 1533V. Conclusion 1534VI. Acknowledgments 1534VII. References 1534
517 citations
430 citations
TL;DR: This research presents a novel and scalable approach called “Smartphone Drug Targeting” that allows for real-time decision-making and real-world application in the field of drug discovery and development.
Abstract: [Song, Zhen-Lei] Sichuan Univ, Key Lab Drug Targeting, Educ Minist, Dept Med Chem,W China Sch Pharm, Chengdu 610041, Peoples R China
345 citations
TL;DR: Introduction 13103 CationicSequences 13104 Anionic Sequences 13106 3a.
339 citations