Explorations on the Asymmetric Total Synthesis of Isoschizogamine

Zhou, Jianguang; Magomedov, Nabi A.

doi:10.1021/jo070144x

Cited by 30 publications

(14 citation statements)

References 26 publications

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“…In this context, N ‐acyl vinylaziridines 25 has been successfully converted into the corresponding 7‐membered lactams ( 27 ) through ACR‐induced ring expansion (Scheme A) . This strategy was used for the synthesis of an isoschizozygane alkaloid (Scheme B) . However, the original conditions reported by Lindström and Somfai (LHMDS, THF, −78 to 0 °C) did not promote the expected rearrangement of substrate 28 ; instead, the desired 7‐membered lactam ( 29 ) was produced by heating (80 °C) in toluene after deprotonation (LHMDS, toluene, −78 °C, 30 min).…”

Section: Acr‐induced Ring‐expansion Strategies For the Synthesis Of Mmentioning

confidence: 99%

Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies

2017

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The aza-Claisen rearrangement,a lso known as the 3-aza-Coper earrangement, has attracted significant attention because it can be used as ac omplimentarym ethodt o access ad iverse range of useful organic molecules. The presence of an itrogen atom at the 3-position enables the tethering of various-sized azacycles, thereby giving ring-expansion strategiest hat take advantage of the aza-Claisen rearrangementadistinct advantage comparedt oo ther [3,3]-sigmatropic rearrangements. Recent advances in aza-Claisen rearrangements have facilitatedo therwise-inaccessible ring expansions in ah ighly stereoselective manner. The utility of aza-Claisen-rearrangement-induced ring-expansion strategies has been exemplified in the synthesis of ad iverse range of naturalp roducts. This Focus Review summarizes recent advancesi na za-Claisen-rearrangement-induced ring-expansion strategy, in particular applicationsi nt he synthesis of bioactive alkaloids.

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Section: Acr‐induced Ring‐expansion Strategies For the Synthesis Of Mmentioning

confidence: 99%

Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies

2017

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“…The high optical purity (97% ee) shows that the stereochemistry of the aziridine was transferred to the quaternary center with high fidelity (Scheme 13). 29…”

Section: Scheme 12mentioning

confidence: 99%

Recent Advances in the Aza-Claisen Rearrangement

Majumdar¹,

Bhattacharyya²,

Chattopadhyay³

et al. 2009

Synthesis

102

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This brief review article describes developments in the aza-Claisen rearrangement over the last nine years. In this article, the emphasis has been given to the various aspects of the aza-Claisen rearrangement, especially metal-mediated stereoselective transformation, zwitterionic aza-Claisen rearrangement and microwave-assisted aza-Claisen rearrangement. 1 Introduction 2 Definition and Overview 3 Thermal Aza-Claisen Rearrangement 4 Catalysis of the Aza-Claisen Rearrangement 4.1 Catalysis by Boron Reagents 4.2 Catalysis by Palladium Reagents 4.3 Catalysis by Gold Salts 4.4 Catalysis by Ruthenium Salts 4.5 Catalysis by Zinc(II) Chloride 5 Zwitterionic Aza-Claisen Rearrangement 6 Microwave-Assisted Aza-Claisen Rearrangement 7 Miscellaneous 8 Conclusions

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“…To date, one racemic total synthesis by Heathcock and two synthetic studies have been reported. [54][55][56][57][58] Chart 4 depicts our synthesis of isoschizogamine. Oxidation of exo-norborneol (48) and a subsequent reaction with trisyl hydrazide afforded hydrazone 49.…”

Section: Synthesis Of Isoschizogaminementioning

confidence: 99%

Synthesis of Natural Products with Polycyclic Systems

Yokoshima

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Herein we present our unique strategies to synthesize natural products. To prepare mersicarpine, an atypical indole alkaloid, our procedure features an Eschenmoser-Tanabe fragmentation to synthesize an alkyne unit, a combination of a Sonogashira coupling and a gold(III) catalyzed cyclization to construct the indole skeleton, and a one-pot process to arrange the cyclic imine and the hemiaminal moieties. Additionally, we synthesized a frog poison, histrionicotoxin, via a chirality transfer from an allenylsilane to prepare a pseudosymmetrical dienyne, dienyne metathesis to produce an optically active bicyclo [5.4.0] system, and an asymmetric propargylation. To synthesize lyconadin A, a Lycopodium alkaloid, a combination of an azaPrins reaction and electrocyclic ring opening constructed the highly fused tetracyclic compound. The synthesis of isoschizogamine features a facile construction of the carbon framework through a Wagner-Meerwein rearrangement, a tandem metathesis, a stereoselective rhodium-mediated 1,4-addition of an arylboronic acid, and a ring-closing metathesis via a hemiaminal ether.

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Explorations on the Asymmetric Total Synthesis of Isoschizogamine

Cited by 30 publications

References 26 publications

Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies

Advances in Aza‐Claisen‐Rearrangement‐Induced Ring‐Expansion Strategies

Recent Advances in the Aza-Claisen Rearrangement

Synthesis of Natural Products with Polycyclic Systems

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