Chiral pools have been commonly utilized as inexpensive and versatile building blocks in organic synthesis.In this account,we provide an overview of our recent synthetic efforts toward polycyclic natural products usin...Chiral pools have been commonly utilized as inexpensive and versatile building blocks in organic synthesis.In this account,we provide an overview of our recent synthetic efforts toward polycyclic natural products using chiral natural small molecules(chiral pool)as starting materials.Key achievements during our syntheses include intermolecular Diels-Alder/intramolecular hetero-Diels-Alder cascade to enable modification of previously proposed biosynthetic pathway of bolivianine,Diels-Alder-type dimerization through a conjugated furanyl diene intermediate to achieve three types of lindenane[4+2]dimers,Iron-catalyzed reductive aldol reaction to construct core of rumphellclovane E and[3,3]-rearrangement along with vinylo-gous Pummerer rearrangement to make epoxyquinol substructure of JBIR-23/-24.In the final,the outlook is also presented.展开更多
1 Introduction Ionic liquids(Ils)are low melting point salts,which are characterized by properties such as high ability to dissolve organic,organometallic and even inorganic compounds,absence of flammability,lack of m...1 Introduction Ionic liquids(Ils)are low melting point salts,which are characterized by properties such as high ability to dissolve organic,organometallic and even inorganic compounds,absence of flammability,lack of measurable vapour pressure and high thermal stability.Due to these peculiar properties,they have recently attracted considerable attention as greener alternatives to volatile organic solvents.A few chiral ionic liquids,which could provide a renewal in the field of chiral solvents,have also been reported recently.Herein,we will present the synthesis of a new family of ionic liquids based on a thiazolinium skeleton.Preliminary results on the use of these chiral ionic liquids in the field of chiral recognition and organic synthesis will also be reported.展开更多
Based on chiral pool strategy,a synthesis of the C1-C9 domain of the proposed structure of didemnaketal A,a natural product with potent HIV-1 protease inhibitory activity,has been achieved.Key transformations are a Sh...Based on chiral pool strategy,a synthesis of the C1-C9 domain of the proposed structure of didemnaketal A,a natural product with potent HIV-1 protease inhibitory activity,has been achieved.Key transformations are a Shar-pless asymmetric dihydroxylation and a chelation-controlled allylation.展开更多
A synthesis of(R)-muscone(1),a valuable musk odorant,is presented.The stereogenic center of muscone was introduced from methyl(R)-5-bromo-4-methylpentanoate(5),a chiral pool molecule developed in our group,and the mac...A synthesis of(R)-muscone(1),a valuable musk odorant,is presented.The stereogenic center of muscone was introduced from methyl(R)-5-bromo-4-methylpentanoate(5),a chiral pool molecule developed in our group,and the macrocyclic ring was prepared by ring-closing metathesis(RCM)reaction.展开更多
Starting from chiral methyl molecules 3 and 4,both derived from(R)-4-methyl-δ-valerolactone,we have ac-complished the synthesis of(R)and(S)-3-methylheptanoic acids.Our methods are amendable to the syntheses of a wide...Starting from chiral methyl molecules 3 and 4,both derived from(R)-4-methyl-δ-valerolactone,we have ac-complished the synthesis of(R)and(S)-3-methylheptanoic acids.Our methods are amendable to the syntheses of a wide variety of chiral 3-methyl alkanoic acids.展开更多
基金We thank financial support from the NSFC of China(21925106,21901170)Department of Science and Technology of Sichuan Province(2019JDTD0020).
文摘Chiral pools have been commonly utilized as inexpensive and versatile building blocks in organic synthesis.In this account,we provide an overview of our recent synthetic efforts toward polycyclic natural products using chiral natural small molecules(chiral pool)as starting materials.Key achievements during our syntheses include intermolecular Diels-Alder/intramolecular hetero-Diels-Alder cascade to enable modification of previously proposed biosynthetic pathway of bolivianine,Diels-Alder-type dimerization through a conjugated furanyl diene intermediate to achieve three types of lindenane[4+2]dimers,Iron-catalyzed reductive aldol reaction to construct core of rumphellclovane E and[3,3]-rearrangement along with vinylo-gous Pummerer rearrangement to make epoxyquinol substructure of JBIR-23/-24.In the final,the outlook is also presented.
文摘1 Introduction Ionic liquids(Ils)are low melting point salts,which are characterized by properties such as high ability to dissolve organic,organometallic and even inorganic compounds,absence of flammability,lack of measurable vapour pressure and high thermal stability.Due to these peculiar properties,they have recently attracted considerable attention as greener alternatives to volatile organic solvents.A few chiral ionic liquids,which could provide a renewal in the field of chiral solvents,have also been reported recently.Herein,we will present the synthesis of a new family of ionic liquids based on a thiazolinium skeleton.Preliminary results on the use of these chiral ionic liquids in the field of chiral recognition and organic synthesis will also be reported.
文摘Based on chiral pool strategy,a synthesis of the C1-C9 domain of the proposed structure of didemnaketal A,a natural product with potent HIV-1 protease inhibitory activity,has been achieved.Key transformations are a Shar-pless asymmetric dihydroxylation and a chelation-controlled allylation.
文摘A synthesis of(R)-muscone(1),a valuable musk odorant,is presented.The stereogenic center of muscone was introduced from methyl(R)-5-bromo-4-methylpentanoate(5),a chiral pool molecule developed in our group,and the macrocyclic ring was prepared by ring-closing metathesis(RCM)reaction.
文摘Starting from chiral methyl molecules 3 and 4,both derived from(R)-4-methyl-δ-valerolactone,we have ac-complished the synthesis of(R)and(S)-3-methylheptanoic acids.Our methods are amendable to the syntheses of a wide variety of chiral 3-methyl alkanoic acids.
