Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2022; 54(13): 3093-3104
DOI: 10.1055/a-1773-4386
DOI: 10.1055/a-1773-4386
paper
Asymmetric Total Synthesis of Ventilanones A and B, Two Naturally Occurring Pyranonaphthoquinones from Ventilago harmandiana
We are grateful for the financial support from the NSRF through the Program Management Unit for Human Resources & Institutional Development, Research and Innovation [B16F640099], the Center of Excellence for Innovation in Chemistry (PERCH-CIC), the Ministry of Higher Education, Science, Research and Innovation, and Mahidol University under the National Research Universities Initiative.
Abstract
The asymmetric synthesis of the novel pyranonaphthoquinones ventilanone A and ventilanone B, isolated from the Thai endemic plant Ventilago harmandiana, is accomplished by employing l-rhamnose and gallic acid as the starting materials. The key reactions are the utilization of a newly introduced reagent, PhSCF2H/SnCl4, for the formylation of sterically hindered aromatics containing an electron-withdrawing methyl ester, and the efficient Hauser annulation of phenylthiophthalides with optically active C-1 glycals derived from l-rhamnose. The developed synthetic methodologies solve the long-standing problem of the formylation of sterically hindered aromatics containing electron-withdrawing groups, and are applicable for the synthesis of other analogues with substituents on the aromatic and pyran rings.
Key words
total synthesis - Hauser annulation - pyranonaphthoquinones - natural products - Ventilago harmandiana Pierre - ventilanonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1773-4386.
- Supporting Information
Publication History
Received: 25 January 2022
Accepted after revision: 16 February 2022
Accepted Manuscript online:
16 February 2022
Article published online:
07 April 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Yeo W.-H, Yun B.-S, Back N.-I, Kim Y.-H, Kim S.-S, Park E.-K, Whang K.-S, Yu S.-H. J. Antibiot. 1997; 50: 546
- 2 Krishnakumari G, Bhuvaneswari B, Swapna IR. Fitoterapia 2001; 72: 671
- 3a Brimble M, Nairn M, Duncalf L. Nat. Prod. Rep. 1999; 16: 267
- 3b Brimble MA. Pure Appl. Chem. 2000; 72: 1635
- 4 Giles RG, Green IR, van Eeden N. Synthesis 2004; 1601
- 5 Naysmith BJ, Hume PA, Sperry J, Brimble MA. Nat. Prod. Rep. 2017; 34: 25
- 6a Balakrishnan N, Singh B. Asian J. Chem. 2013; 25: 2438
- 6b Periyasamy K, Kaliyaperumal S. Int. J. Curr. Pharm. Res. 2016; 8: 16
- 6c Caichompoo W, Zhang Q.-Y, Thangthaisong T, Phadungkit M. Int. J. Pharm. Res. 2012; 89
- 6d Lipipun V, Kurokawa M, Suttisri R, Taweechotipatr P, Pramyothin P, Hattori M, Shiraki K. Antiviral Res. 2003; 60: 175
- 7a Jammula SR, Pepalla SB, Telikepalli H, Rao KJ, Thomson RH. Phytochemistry 1991; 30: 3741
- 7b Lin L.-C, Chou C.-J, Kuo Y.-C. J. Nat. Prod. 2001; 64: 674
- 7c Hanumaiah T, Marshall DS, Rao B, Rao C, Rao G, Rao J, Rao K, Thomson RH. Phytochemistry 1985; 24: 2373
- 8 OTOP, Herbal Medicine of Sakai Tribe, 2015 (accessed Mar 29, 2022), see: http://otopphatthalung.blogspot.com/2015/11/blog-post_8.html
- 9a Panthong A, Kanjanapothi D, Taesotikul T, Phankummoon A, Panthong K, Reutrakul V. J. Ethnopharmacol. 2004; 91: 237
- 9b Molee W, Phanumartwiwath A, Kesornpun C, Sureram S, Ngamrojanavanich N, Ingkaninan K, Mahidol C, Ruchirawat S, Kittakoop P. Chem. Biodiversity 2018; 15: 1700537
- 10 Panthong K, Hongthong S, Kuhakarn C, Piyachaturawat P, Suksen K, Panthong A, Chiranthanut N, Kongsaeree P, Prabpai S, Nuntasaen N. Phytochemistry 2020; 169: 112182
- 11 Brimble MA, Nairn MR, Prabaharan H. Tetrahedron 2000; 56: 1937
- 12 Kongsriprapan S, Kuhakarn C, Deelertpaiboon P, Panthong K, Tuchinda P, Pohmakotr M, Reutrakul V. Pure Appl. Chem. 2012; 84: 1435
- 13 Deshpande PP, Price KN, Baker DC. J. Org. Chem. 1996; 61: 455
- 14 Deelertpaiboon P, Reutrakul V, Jarussophon S, Tuchinda P, Kuhakarn C, Pohmakotr M. Tetrahedron Lett. 2009; 50: 6233
- 15 Zhao C, Chen J, Cao D, Wang J, Ma W. Tetrahedron 2019; 75: 1997
- 16 Fogagnolo M, Bergamini P, Marchesi E, Marvelli L, Gambari R, Lampronti I. New J. Chem. 2020; 44: 12227
- 17a Soleymaniahooie T. Res. J. Recent Sci. 2015; 4: 80
- 17b Bering L, Jeyakumar K, Antonchick AP. Org. Lett. 2018; 20: 3911
- 18 Xie Y.-D, Liu J.-P, Wang W, Shi Y.-H, Wang X.-P, Sun M, Xu X.-Y, Li N. Bioorg. Med. Chem. 2020; 30: 127277
- 19 Saadati F, Meftah-Booshehri H. Synlett 2013; 24: 1702
- 20 Oguma T, Katsuki T. J. Am. Chem. Soc. 2012; 134: 20017
- 21 Alam A, Takaguchi Y, Ito H, Yoshida T, Tsuboi S. Tetrahedron 2005; 61: 1909
- 22 Betterley NM, Kongsriprapan S, Chaturonrutsamee S, Deelertpaiboon P, Surawatanawong P, Pohmakotr M, Soorukram D, Reutrakul V, Kuhakarn C. Synthesis 2018; 50: 2033
- 23a Claessens S, Jacobs J, De Kimpe N. Synlett 2007; 741
- 23b Mal D, Ray S, Sharma I. J. Org. Chem. 2007; 72: 4981
- 23c Kraus GA, Dong P. Nat. Prod. Commun. 2015; 10: 1025
- 23d Chakraborty S, Das G, Ghosh S, Mal D. Org. Biomol. Chem. 2016; 14: 10636
- 24a Janata M, Lochmann L, Müller AH. Macromol. Chem. Phys. 1993; 194: 625
- 24b Van Beylen M, Van Lierde P, Zimm BH, Szwarc M. Macromol. Rapid Commun. 1997; 18: 113
- 25 Srikrishna A, Reddy TJ, Viswajanani R. Tetrahedron 1996; 52: 1631
- 26 Hashmat Ali M, Niedbalski M, Bohnert G, Bryant D. Synth. Commun. 2006; 36: 1751