Rearrangement of a Tricyclic 2,5-Cyclohexadienone: Towards a General Synthetic Route to the Daphnanes and (+)-Resiniferatoxin

Jackson, Stona R.; Johnson, Michael G.; Mikami, Masafumi; Shiokawa, Sojiro; Carreira, Erick M.

doi:10.1002/1521-3773(20010716)40:14<2694::aid-anie2694>3.0.co;2-d

Cited by 67 publications

(22 citation statements)

References 24 publications

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“…[26] . 2001 年, Carreira 课题 [22a] 图式 7 Carreira 课题组 Resiniferatoxin 的骨架构建研究 Scheme 7 Skeleton construction study of Resiniferatoxin by Carreira et al [27] 重排的前体 …”

Section: 'mentioning

confidence: 99%

Application of Photochemical Rearrangement of Santonin in Total Synthesis of Complex Natural Terpenoids

Yang¹,

Gao²

2018

Acta Chim. Sinica

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Terpenoids represent one of the largest and most diverse classes of secondary metabolites and widely exist in nature. Among them, sesquiterpene lactones are ubiquitous in a variety of medicinal plants, which are the main active ingredients of many traditional Chinese herbal medicines. However, it is extremely challenging to accomplish the total synthesis of these natural compounds. Photochemical rearrangement of santonin is an effective strategy to construct the guaianolide skeleton. Furthermore, as a renewable natural resource, santonin was extensively used in natural product total synthesis, especially complex terpenoids. In this review, a brief overview of application of photochemical rearrangement of santonin in total synthesis of natural terpenoids is presented, which mainly includes: (1) the synthesis of sesquiterpene and its oligomers, and (2) the core structure construction of some diterpenoids.

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Section: 'mentioning

confidence: 99%

Application of Photochemical Rearrangement of Santonin in Total Synthesis of Complex Natural Terpenoids

Yang¹,

Gao²

2018

Acta Chim. Sinica

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“…58 Several years later, they conducted the first asymmetric total synthesis of a daphnane diterpenoid in 1997. 61 In the same time period, Page's, 56,62,63 Carreira's, 64 West's, 65 and Evan's 66 groups also made tremendous contributions toward the total synthesis of daphnane and tigliane diterpenoids. 60 One year later, they reported an efficient synthesis of the ABC tricyclic core of macrocyclic daphnane diterpenoids, namely 1α-alkyldaphnanes.…”

Section: Synthesis Of Daphnane and Tigliane Diterpenoidsmentioning

confidence: 99%

Recent studies on the chemical constituents of Trigonostemon plants

Yue

2014

Org. Chem. Front.

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“…However, the successful total synthesis of daphnanes has been limited to reports from Wender's group, 18,19) despite extensive synthetic efforts by other research groups. [20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36] We also have been inspired by the formidable structures of daphnanes to launch a synthetic study of 1 as the initial target. This review summarizes our effort to develop a key radicalmediated three-component reaction and its application to the convergent assembly of the tricyclic ABC-ring system of 1.…”

Section: Introductionmentioning

confidence: 99%

Radical-Mediated Three-Component Reaction: A Study toward the Total Synthesis of Resiniferatoxin

Urabe

2015

CHEMICAL & PHARMACEUTICAL BULLETIN

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This review summarizes the efforts to develop a radical-mediated three-component reaction and its application to a convergent approach to synthesize the 5/7/6-tricyclic framework (ABC-rings) of the densely functionalized dephnane diterpene, resiniferatoxin. The α-alkoxy bridgehead radical species, which was designed as the radical donor of the three-component reaction, was generated from O,Se-and O,Te-acetals under two different conditions. The generated α-alkoxy bridgehead radical effectively underwent the threecomponent reaction with α,β-unsaturated ketones and allyltributyltin/aldehyde under each of the conditions, giving rise to a wide variety of multiply functionalized 2,3-trans disubstituted cyclopentenone moieties. One of the established reactions was utilized as the key assembling reaction of the ABC-tricyclic framework of resiniferatoxin. The reaction of the bridgehead radical of the highly functionalized 6-membered C-ring, the 5-membered A-ring, and an allyltributyltin derivative effectively produced the C4-branched AC-rings. The last B-ring was constructed from the coupling adduct in two steps through the 7-endo cyclization, delivering the tricyclic framework possessing the correct C8 and 9-stereocenters of resiniferatoxin. The present methods demonstrate the power of the three-component reaction using an α-alkoxy bridgehead radical in a convergent approach to the complex architectures of daphnane diterpenes.

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Rearrangement of a Tricyclic 2,5-Cyclohexadienone: Towards a General Synthetic Route to the Daphnanes and (+)-Resiniferatoxin

Cited by 67 publications

References 24 publications

Application of Photochemical Rearrangement of Santonin in Total Synthesis of Complex Natural Terpenoids

Application of Photochemical Rearrangement of Santonin in Total Synthesis of Complex Natural Terpenoids

Recent studies on the chemical constituents of Trigonostemon plants

Radical-Mediated Three-Component Reaction: A Study toward the Total Synthesis of Resiniferatoxin

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