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Literature DB >> 21517105

Use of a tandem Prins/Friedel-Crafts reaction in the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids: formal synthesis of (-)-haouamine A.

Erik Fenster¹, Charlie Fehl, Jeffrey Aubé.

Abstract

A tandem Prins/Friedel-Crafts reaction useful for the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids and a formal synthesis of (-)-haouamine A are described.

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Year: 2011 PMID： 21517105 PMCID： PMC3094499 DOI： 10.1021/ol200725m

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

15 in total

1. Synthesis and structure revision of calyxin natural products.

Authors: Xia Tian; James J Jaber; Scott D Rychnovsky
Journal: J Org Chem Date: 2006-04-14 Impact factor: 4.354

2. Formal total synthesis of the cytotoxic marine ascidian alkaloid haouamine A.

Authors: Jeannie H Jeong; Steven M Weinreb
Journal: Org Lett Date: 2006-05-25 Impact factor: 6.005

3. Synthesis of the 3-aza-[7]-paracyclophane core of haouamine A and B.

Authors: Peter Wipf; Markus Furegati
Journal: Org Lett Date: 2006-04-27 Impact factor: 6.005

4. On the origin of the haouamine alkaloids.

Authors: Noah Z Burns; Phil S Baran
Journal: Angew Chem Int Ed Engl Date: 2008 Impact factor: 15.336

5. Formal total synthesis of haouamine A.

Authors: Tsuyoshi Taniguchi; Hisaaki Zaimoku; Hiroyuki Ishibashi
Journal: J Org Chem Date: 2009-03-20 Impact factor: 4.354

6. Simple and one-pot protocol for synthesis of indene-spiro-oxindoles involving tandem Prins and Friedel-Crafts reactions.

Authors: Deevi Basavaiah; Kanumuri Ramesh Reddy
Journal: Org Lett Date: 2007-01-04 Impact factor: 6.005

1. Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.

Authors: R Frederick Lambert; Robert J Hinkle; Stephen E Ammann; Yajing Lian; Jia Liu; Shane E Lewis; Robert D Pike
Journal: J Org Chem Date: 2011-10-25 Impact factor: 4.354

1 in total

Use of a tandem Prins/Friedel-Crafts reaction in the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids: formal synthesis of (-)-haouamine A.

1. Synthesis and structure revision of calyxin natural products.

2. Formal total synthesis of the cytotoxic marine ascidian alkaloid haouamine A.

3. Synthesis of the 3-aza-[7]-paracyclophane core of haouamine A and B.

4. On the origin of the haouamine alkaloids.

5. Formal total synthesis of haouamine A.

6. Simple and one-pot protocol for synthesis of indene-spiro-oxindoles involving tandem Prins and Friedel-Crafts reactions.

7. Synthetic studies toward the haouamines.

8. Haouamines A and B: a new class of alkaloids from the ascidian Aplidium haouarianum.

9. Much improved conditions for the Negishi cross-coupling of iodoalanine derived zinc reagents with aryl halides.

10. Scalable total synthesis and biological evaluation of haouamine A and its atropisomer.

1. Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.