Total Synthesis of Hirsutellone B

Nicolaou, K. C.; Šarlah, David; Wu, Tingting; Zhan, Weiqiang

doi:10.1002/anie.200903382

Cited by 106 publications

(68 citation statements)

References 23 publications

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“…[65] Nicolaou et al's application of the Black biosynthetic hypothesis [66] in the synthesis of endiandric acids, using a hydrogenation/double-electrocyclisation/Diels-Alder sequence, is a classic. [67] Wender and Howbert's metaphotocycloaddition route to hirsutene, [68] the more recent syntheses of hirsutellone B by Nicolaou et al [69] and Sorensen and coworkers, [70] the double Diels-Alder approaches to FR182877 by Sorenson and coworkers, [71] Evans and Starr, [72] and most recently Nakada and coworkers, [73] and Denmark et al's [4þ2]/[3þ2] domino approach towards daphnilactone B are also outstanding examples. [74] Generation of a reactive ylide from a carbenoid, a strategy pioneered by Padwa from the 1980s, with enantioselective methods emerging from the laboratory of Hodgson, [75] has also proven an effective strategy in the generation of several bonds and significant structural complexity in one step.…”

Section: One-component Domino Reactionsmentioning

confidence: 99%

Multi-Bond Forming Processes in Efficient Synthesis

Green¹,

Sherburn²

2013

Aust. J. Chem.

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An increasing number of synthetic organic chemists are embracing the philosophy of efficiency. Herein we highlight multi-bond forming processes, which form two or more new covalent bonds in a single synthetic operation. Such processes, which have the ability to rapidly increase structural complexity, are preeminent in contemporary synthetic organic chemistry. In this short review we classify, analyse, and contrast contemporary multi-bond forming processes, frame these cutting edge contributions within a historical context, and speculate on likely future developments in the area.

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Section: One-component Domino Reactionsmentioning

confidence: 99%

Multi-Bond Forming Processes in Efficient Synthesis

Green¹,

Sherburn²

2013

Aust. J. Chem.

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“…There is still no biomimetic total synthesis of hirsutellones with regard of the construction of the 6,5,6-fused tricyclic moiety. However, Nicolaou's total synthesis of hirsutellone B (118) [90] is remarkably reminiscent of Oikawa's cascade cyclization leading to the GKK1032A 2 carbocyclic core (Scheme 14.29) [88]. Starting from the epoxide intermediate 131, electrophilic activation in the presence of Et 2 AlCl provided diastereoselectively the tricyclic core 134 of hirsutellones in 50% yield.…”

Section: A Metalated Ionophore Template For the Biomimetic Synthesis mentioning

confidence: 99%

Biomimetic Synthesis of Non‐Aromatic Polycyclic Polyketides

Nay

Riache

2011

Biomimetic Organic Synthesis

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“…3 In this communication, we report the in situ generation of this 17,1′-dehydrohirsutellone B ( 5 ) and its conversion to hirsutellones A ( 1 ), B ( 2 ) and C ( 3 ), thereby confirming the Isaka hypothesis and achieving the first total synthesis of hirsutellones A ( 1 ) and C ( 3 ) and a second generation total synthesis of hirsutellone B ( 2 ). 4,5 These natural products are notable not only for their novel molecular architectures, but also for their promising antituberculosis properties (active against Mycobacterium tuberculosis , MIC = 0.78 μg/mL for 1 – 3 ). 1 …”

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confidence: 99%