Total Synthesis of (+)-Sundiversifolide

Yokoe, Hiromasa; Sasaki, Hiroyuki; Yoshimura, Tetsuzo; Shindo, Mitsuru; Yoshida, Masahiro; Shishido, Kozo

doi:10.1021/ol062960h

Cited by 42 publications

(17 citation statements)

References 12 publications

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“…Chemical studies of Helianthus annuus have shown that this species is a rich source of terpenes, 4) and particularly of sesquiterpenes, e.g., heliananes (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13) and sundiversifolide (14), [5][6][7][8] with a wide spectrum of biological activities, including potential allelopathic activity. The ionone-type bisnorsesquiterpenes (15,16) 9,10) have been isolated from rattail fescue (Vulpia myuros) and identified as allelochemicals 11) and the meroterpenes breviones (17)(18)(19), isolated from Penicillium brevicompactum Dierckw, have also been identified as allelochemicals.…”

Section: Synthesis Of Natural Products With Allelopathic Activitymentioning

confidence: 99%

Stereocontrolled Total Synthesis of Natural Products with Characteristic Molecular Structures and Biological Activities

Shishido

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Total synthetic studies on natural products with promising biological profiles, coupled with their intriguing structural features, are described. The target molecules dealt with in this article are five heliananetype sesquiterpenes (heliannuols A, D and K and heliespirones A and C) and three meroterpenes (breviones A, B and C) with allelopathic activity, as well as four cytotoxic polyketides (lasonolide A and aspergillides A, B and C) and two pyrrolidinoindoline alkaloids (physostigmine and psychotrimine) with acetylcholine esterase inhibitory and antibacterial activities.

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Section: Synthesis Of Natural Products With Allelopathic Activitymentioning

confidence: 99%

Stereocontrolled Total Synthesis of Natural Products with Characteristic Molecular Structures and Biological Activities

Shishido

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Owing to the relatively limited number of reports on synthetic studies of xanthanolides, the development of an ef cient synthetic strategy is needed in order to not only supply these natural products, but also identify their biological targets and develop related drugs. 2 The RCM method has been considered as the rst choice to design a synthetic strategy for seven membered ring construction, and Morken, 3 Martin, 4 and Shishido, 5 as well as our group 6 reported the synthesis of xanthanolides using the RCM method including enyne metathesis. 7 However, developing transition metal free methodologies should be no less important than the RCM method from the perspective of natural resources issues as well as the diversity of synthetic methodologies.…”

Section: Total Synthesis Of Xanthanolidesmentioning

confidence: 99%

Synthesis of Xanthanolides Including New Acylations and Their Synthetic Applications

Shindo¹,

Matsumoto²

2013

J. Synth. Org. Chem. Jpn.

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“…and divided into two groups according to the configuration of their cis-and trans-ring junctions. Representative examples of the cis-fused xanthanolides are the sundiversifolide (4), [7][8][9][10]11) the diversifolide (5) 10,12) and the 8-epi-xanthatin (9) 11,13,14) ; xanthatin (7) 11,15) and 11α,13-dihydroxanthatin (8) belong to the trans series. 11,16) They are known for their wide variety of interesting allelopathic, 17) cytotoxic, 18) anti-leishmanial, 19) and anti-MRSA activity.…”

Section: Multidrug-resistant Pathogens Such As Methicillin-resistantmentioning

confidence: 99%

Enantioselective Synthesis of 8-<i>epi</i>-Xanthatin and Biological Evaluation of Xanthanolides and Their Derivatives

et al. 2012

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An enantioselective synthesis of 8-epi-xanthatin (9) has been accomplished starting from the bicyclic lactone 3, which has been used for the synthesis of other xanthanolides, sundiversifolide (4) and diversifolide (5), through a synthetic route without the use of a selenium species. Additionally we have evaluated antimicrobial activities of five natural xanthanolides and their derivatives. Although the synthetic xanthanolides did not show any activity against methicillin-resistant Staphylococcus aureus (MRSA), some of the synthetic intermediates did exhibit moderate antimicrobial activities.Key words xanthanolide; enantioselective synthesis; antimicrobial activity; methicillin-resistant Staphylococcus aureus Multidrug-resistant pathogens such as methicillin-resistant Staphylococcus aureus (MRSA) continue to pose clinical challenges. 1,2) Recently the emergence of community-acquired MRSA has compounded the problem 3,4) and focused increased attention on efforts to develop new anti-MRSA drugs.In 1997, Sato et al. 5) reported that xanthatin (7), a member of the xanthanolides, 6) a sesquiterpene family possessing the characteristic oxabicyclo[5.3.0] decene core as its common basic carbon framework, exhibited potent anti-MRSA activity with an MIC value of 7.8 µg/mL. Xanthanolide sesquiterpenes were isolated from Helianthus annuus L. or Xanthium sp. and divided into two groups according to the configuration of their cis-and trans-ring junctions. Representative examples of the cis-fused xanthanolides are the sundiversifolide (4), 7-10,11) the diversifolide (5) 10,12) and the 8-epi-xanthatin (9) 11,13,14) ; xanthatin (7) 11,15) and 11α,13-dihydroxanthatin (8) belong to the trans series. 11,16) They are known for their wide variety of interesting allelopathic, 17) cytotoxic, 18) anti-leishmanial, 19) and anti-MRSA activity.5) As part of our ongoing program directed towards the synthesis of xanthanolides, we have established an efficient access to both cis-and trans-xanthanolides starting from the bicyclic lactone 2 with a cis ring juncture, which can be prepared from the Evans aldol adduct 1 as the common key intermediate in an optically pure form, and have achieved the total synthesis of four xanthanolides, 4, 5, 6 and 7. In this report we describe an enantioselective synthesis of 8-epi-xanthatin (9) starting from 3, which is the intermediate for 4 and 5, and the biological evaluation of the compound library including the five xanthanolides and their derivatives (Chart 1).8-epi-Xanthatin (9), commonly isolated from the extracts of the aerial parts of various species in the genus Xanthium, has also been obtained upon elimination of acetic acid from xanthumin (8-epi-2-acetoxy-3-hydroxanthatin). It has been shown Note * To whom correspondence should be addressed. e-mail: shishido@ph.tokushima-u.ac.jp 12) total synthesis of 1. In our previous synthesis of xanthatin (7), 15) which possesses a similar basic carbon framework and functionalities except for the stereochemistry on the ring junction, we employed two types of syn...

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Total Synthesis of (+)-Sundiversifolide

Cited by 42 publications

References 12 publications

Stereocontrolled Total Synthesis of Natural Products with Characteristic Molecular Structures and Biological Activities

Stereocontrolled Total Synthesis of Natural Products with Characteristic Molecular Structures and Biological Activities

Synthesis of Xanthanolides Including New Acylations and Their Synthetic Applications

Enantioselective Synthesis of 8-<i>epi</i>-Xanthatin and Biological Evaluation of Xanthanolides and Their Derivatives

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