Synthesis of C1–C9 Domain of the Nominal Didemnaketal A

Zhang, Shunji; Shi, Yong; Tian, Weisheng

doi:10.1002/cjoc.201500256

Cited by 4 publications

(2 citation statements)

References 23 publications

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“…Moreover, the concept of “ from nature to nature ” was applied in our asymmetric synthesis of proposed apratoxin E ( 30 S -7 ). In other words, the key fragment 9 could be prepared from industrial waste 10 , and another fragment 11 could be derived from glutamic acid.…”

Section: Resultsmentioning

confidence: 99%

“…The preparation of nonpeptide fragment 9 is shown in Scheme . Chiral lactone 10 was isolated from the industrial wastewater during the degradation of saponin glycosides in 22% yield. Treatment of 10 with benzyl chloride (BnCl) and NaOH in toluene under refluxing conditions resulted in the ring opening and simultaneous selective benzylation of the primary alcohol .…”

Section: Resultsmentioning

confidence: 99%

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Divergent Synthesis of Revised Apratoxin E, 30-epi-Apratoxin E, and 30S/30R-Oxoapratoxin E

Mao

Liu

et al. 2017

J. Org. Chem.

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In this report, originally proposed apratoxin E (30S-7), revised apratoxin E (30R-7), and (30S)/(30R)-oxoapratoxin E (30S)-38/(30R)-38 were efficiently prepared by two synthetic methods. The chiral lactone 10, recycled from the degradation of saponin glycosides, was utilized to prepare the key nonpeptide fragment 9. Our alternative convergent assembly strategy was applied to the divergent synthesis of revised apratoxin E and its three analogues. Moreover, ring-closing metathesis (RCM) was for the first time found to be an efficient strategy for the macrocyclization of apratoxins.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Divergent Synthesis of Revised Apratoxin E, 30-epi-Apratoxin E, and 30S/30R-Oxoapratoxin E

Mao

Liu

et al. 2017

J. Org. Chem.

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Novel Total Synthesis of Mansouramycin B

et al. 2016

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A novel total synthesis of Mansouramycin B (1) was performed via 10 steps in 28% overall yield starting from the readily available and cheap salicylaldehyde. Two key steps of this total synthesis are noteworthy. The first one is base‐promoted one‐pot aerobic aromatization of N‐tosyltetrahydroisoquinoline 6, the second one is oxidation of 5‐hydroxy‐3‐methyl‐isoquinoline 8 with iodobenzene diacetate [PhI(OAc)2].

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