Total Syntheses of Pancratistatin. A Review

Manpadi, Madhuri; Kornienko, Alexander

doi:10.1080/00304940809458083

Cited by 56 publications

(24 citation statements)

References 92 publications

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“…After completing the functionalization of the C ring, we turned our attention to the construction of the B ring to complete the total synthesis. Banwells modified Bischler-Napieralski reaction, [24] which is thought to proceed via an imino triflate intermediate, has been used widely for closure of the B ring in the synthesis of Amaryllidaceae alkaloids, including trans-dihydronarciclasine (1) and pancratistatin (2). However, literature examples of this reaction show it only to be effective for primary alkyl carbamate substrates.…”

Section: B-ring Construction Under Banwells Modified Bischler-napieramentioning

confidence: 99%

“…Based on their potent and selective anticancer activity, as well as their unique structural features, Amaryllidaceae isocarbostyril alkaloids have been an attractive synthetic target for the last two decades. [1,2] Some representative members of this class of natural products are trans-dihydronarciclasine (1), pancratistatin (2), lycoricidine (3), and narciclasine (4, Figure 1). These natural isocarbostyrils exhibit potent cytotoxicity in the NCI 60 human tumor cell line panel with GI 50 values in the nanomolar range.…”

Section: Introductionmentioning

confidence: 99%

“…These natural isocarbostyrils exhibit potent cytotoxicity in the NCI 60 human tumor cell line panel with GI 50 values in the nanomolar range. [3] Although trans-dihydronarciclasine has far greater anticancer activity than the intensively investigated pancratistatin (2) and other congeners, [3b] less effort has been devoted to biological and synthetic studies on trans-dihydronarciclasine until recently. [4] The isolation of (+)-1 from the Chinese medical plant Zephyranthes candida was reported in 1990.…”

Section: Introductionmentioning

confidence: 99%

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Stereocontrolled Total Synthesis of (+)‐trans‐Dihydronarciclasine

Hwang¹,

Kim²,

Kim³

2012

Chemistry A European J

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A highly stereoselective and efficient total synthesis of trans-dihydronarciclasine from a readily available chiral starting material was developed. The synthesis defines two of the five stereogenic centers of the natural product by an amino acid ester-enolate Claisen rearrangement. The other three stereogenic centers are created in a highly stereocontrolled fashion via a six-ring vinylogous ester intermediate, which is generated from the γ,δ-unsaturated ester functional group of the Claisen rearrangement product in an efficient three-step sequence. This concise total synthesis exemplifies the use of a highly regioselective Friedel-Crafts-type cyclization to form the B ring via an isocyanate intermediate derived from an N-Boc group, which is superior to the conventional method using an imino triflate intermediate. This same N-Boc group is employed to give high selectivity in the Claisen rearrangement earlier in the sequence.

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Section: B-ring Construction Under Banwells Modified Bischler-napieramentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Stereocontrolled Total Synthesis of (+)‐trans‐Dihydronarciclasine

Hwang¹,

Kim²,

Kim³

2012

Chemistry A European J

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“…These compounds, and their 7-deoxy derivatives, 7-deoxypancratistatin ( 2 ) and lycoricidine ( 4 ), have been the focus of many synthetic ventures in the last three decades. 1 Many unnatural or truncated derivatives of pancratistatin have been prepared and evaluated for biological activity with the intent to produce more bioavailable agents then the highly water-insoluble natural products. 2 …”

mentioning

confidence: 99%

“…Modifications of narciclasine, one of the most potent of Amaryllidaceae constituents, 1d are less common. 2b,3 …”

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confidence: 99%

Synthesis and biological evaluation of unnatural derivatives of narciclasine: 7-aza-nornarciclasine and its N-oxide

Vshyvenko

Reisenauer

Rogelj

et al. 2014

Bioorganic & Medicinal Chemistry Letters

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Several unnatural derivatives of narciclasine were prepared in which the C-7 carbon was replaced with nitrogen. The 7-aza derivative and its N-oxide were prepared by the coupling of iodopicolinic acid with a conduramine unit derived chemoenzymatically from bromobenzene. Intramolecular Heck reaction was used to construct the carbostyryl ring system. The compounds were submitted to biological screening against cancer cell lines. Full experimental and spectra data are provided for all new compounds.

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