Synthesis of 6-deoxo-24-epiteasterone and its analogs

Article abstract of DOI:10.1134/S1070428006090120

Selective reduction of the C⁸=C¹⁴ double bond in 3-hydroxyergosta-8(14),22-dien-15-one, followed by cis-hydroxylation of the double bond in the side chain and reduction of the 15-oxo group gave new 3β-hydroxy-6-deoxobrassinosteroids, their 22S,23S isomers, and the corresponding esters. The side chain in the products is identical to that in such known natural brassinosteroids as 24-epibrassinolide and 24-epicastasterone.

Full text of DOI:10.1134/S1070428006090120

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ꢄ ꢄꢀꢀꢄ+]ꢋꢅꢄꢊꢍꢌꢈꢄPꢄꢉꢀ+ꢅꢄꢁꢇ+ꢅꢄ- ꢄ ꢄꢂꢆꢄ+]ꢋꢍꢄ
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ꢍꢃꢈꢄWꢄꢉꢀ+ꢅꢄꢂꢂꢇ+ꢅꢄ-ꢄ ꢄꢌꢄ+]ꢋꢅꢄꢊꢍꢌꢈꢄPꢄꢉꢀ+ꢅꢄꢁꢇ+ꢅꢄ- ꢄ ꢄꢄ & +ꢅꢄ-ꢄ ꢄꢎꢄ+]ꢋꢅꢄꢀꢍꢆꢃꢄGꢄꢉꢁ+ꢅꢄ& +ꢅꢄ-ꢄ ꢄꢌꢄ+]ꢋꢅꢄꢂꢍꢆꢂꢄVꢄ
ꢂꢆꢄ+]ꢋꢍꢄ &ꢄ105ꢄVSHFWUXPꢅꢄ ꢅꢄSSPꢒꢄꢀꢆꢍꢏꢂꢄTꢄꢉ& ꢋꢅꢄ ꢉꢁ+ꢅꢄ2$FꢋꢅꢄꢂꢍꢆꢁꢄVꢄꢉꢁ+ꢅꢄ2$FꢋꢅꢄꢂꢍꢆꢎꢄVꢄꢉꢁ+ꢅꢄ2$Fꢋꢅꢄꢄ
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ꢅꢄSSPꢒꢄꢀꢆꢍꢈꢃꢄTꢄꢉ& ꢋꢅꢄꢀꢂꢍꢂꢃꢄTꢄꢉ& ꢋꢅꢄꢀꢂꢍꢎꢌꢄTꢄꢉ& ꢋꢅꢄ
ꢊꢆꢍꢂꢎꢄGꢄꢉ& ꢋꢅꢄꢁꢏꢍꢏꢏꢄWꢄꢉ& ꢋꢅꢄꢊꢀꢍꢃꢈꢄGꢄꢉ& ꢋꢅꢄꢊꢀꢍꢎꢏꢄWꢄ ꢀꢁꢍꢏꢏꢄTꢄꢉ& ꢋꢅꢄꢀꢎꢍꢀꢏꢄTꢄꢉ& ꢋꢅꢄꢂꢆꢍꢈꢎꢄWꢄꢉ& ꢋꢅꢄꢂꢆꢍꢏꢌꢄTꢄ
ꢉ& ꢋꢅꢄꢊꢂꢍꢁꢌꢄVꢄꢉ& ꢋꢅꢄꢊꢊꢍꢎꢀꢄGꢄꢉ&ꢋꢅꢄꢊꢈꢍꢂꢀꢄGꢄꢉ& ꢋꢅꢄꢃꢁꢍꢈꢊꢄGꢄ ꢉ&2&+ ꢋꢅꢄꢂꢀꢍꢆꢌꢄTꢄꢉ&2&+ ꢋꢅꢄꢂꢀꢍꢃꢏꢄTꢄꢉ&2&+ ꢋꢅꢄꢄ
ꢉ&ꢋꢅꢄꢌꢃꢍꢈꢏꢄGꢄꢉ& ꢋꢅꢄꢎꢂꢍꢃꢃꢄGꢄꢉ& ꢋꢅꢄꢎꢁꢍꢌꢎꢄGꢄꢉ&ꢋꢅꢄꢎꢌꢍꢁꢂꢄGꢄ ꢂꢂꢍꢃꢃꢄTꢄꢉ& ꢋꢅꢄꢂꢎꢍꢀꢆꢄGꢄꢉ& ꢋꢅꢄꢂꢎꢍꢃꢊꢄWꢄꢉ&ꢋꢅꢄꢂꢈꢍꢂꢆꢄWꢄꢉ&ꢋꢅꢄ
ꢉ& ꢋꢅꢄꢀꢎꢆꢍꢈꢃꢄVꢄꢉ&2&+ꢋꢅꢄꢂꢀꢃꢍꢌꢏꢄVꢄꢉ& ꢋꢍꢄ
ꢁꢆꢍꢌꢆꢄWꢄꢉ&ꢋꢅꢄꢁꢀꢍꢏꢏꢄGꢄꢉ&ꢋꢅꢄꢁꢁꢍꢏꢌꢄWꢄꢉ&ꢋꢅꢄꢁꢃꢍꢌꢈꢄVꢄꢉ& ꢋꢅꢄ
ꢌꢍꢈꢃꢄWꢄꢉ&ꢋꢅꢄꢁꢎꢍꢈꢁꢄGꢄꢉ& ꢋꢅꢄꢁꢏꢍꢏꢎꢄWꢄꢉ& ꢋꢅꢄꢁꢈꢍꢏꢂꢄGꢄꢉ& ꢋꢅꢄ
ꢊꢀꢍꢏꢎꢄWꢄꢉ& ꢋꢅꢄꢊꢂꢍꢂꢆꢄVꢄꢉ& ꢋꢅꢄꢊꢊꢍꢎꢊꢄGꢄꢉ&ꢋꢅꢄꢊꢈꢍꢎꢁꢄGꢄꢉ& ꢋꢅꢄ
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6
<17+(6,6ꢄꢄ2)ꢄꢄꢌꢇ'(2;2ꢇꢂꢊꢇ(3,7($67(521(ꢄꢄ$1'ꢄꢄ,76ꢄꢄ$1$/2*6ꢄꢄ
ꢀꢁꢁꢀꢄ
ꢊꢃꢃ6ꢆꢃꢉ6ꢋꢂꢈꢌꢂ2[RHUJRVWDQHꢂꢉ ꢆꢃꢃꢆꢃꢉꢂWUL\Oꢀ WULꢂ ZDVꢄDGGHGꢅꢄDQGꢄWKHꢄPL[WXUHꢄZDVꢄVWLUUHGꢄIRUꢄꢀꢄKꢅꢄGLOXWHGꢄ
DFHWDWHꢀꢊ;ꢋꢍꢄPSꢄꢀꢂꢎ±ꢀꢂꢈƒ&ꢄꢉIURPꢄ0H2+ꢋꢍꢄ,5ꢄVSHFꢇ ZLWKꢄHWK\OꢄDFHWDWHꢅꢄZDVKHGꢄZLWKꢄDꢄVDWXUDWHGꢄVROXWLRQꢄRIꢄ
WUXPꢄꢉILOPꢋꢅꢄ ꢅꢄFP ꢒꢄꢀꢎꢊꢃꢅꢄꢀꢃꢊꢆꢅꢄꢀꢂꢊꢆꢍꢄ +ꢄ105ꢄVSHFꢇ 1+ &OꢅꢄDQGꢄGULHGꢄRYHUꢄ0J62 ꢍꢄ7KHꢄVROYHQWꢄZDVꢄ
WUXPꢅꢄ ꢅꢄSSPꢒꢄꢆꢍꢎꢂꢄVꢄꢉꢁ+ꢅꢄ& +ꢋꢅꢄꢆꢍꢎꢌꢄGꢄꢉꢁ+ꢅꢄ& +ꢅꢄꢄ UHPRYHGꢅꢄDQGꢄWKHꢄUHVLGXHꢄZDVꢄVXEMHFWHGꢄWRꢄFROXPQꢄ
-
ꢄ ꢄꢎꢄ+]ꢋꢅꢄꢆꢍꢈꢀꢄVꢄꢉꢁ+ꢅꢄ& +ꢋꢅꢄꢆꢍꢈꢂꢄGꢄꢉꢁ+ꢅꢄ& +ꢅꢄ-ꢄ ꢄꢄ FKURPDWRJUDSK\ꢄRQꢄVLOLFDꢄJHOꢄXVLQJꢄF\FORKH[DQH±HWK\Oꢄ
ꢎꢄ+]ꢋꢅꢄꢆꢍꢏꢆꢄGꢄꢉꢁ+ꢅꢄ& +ꢅꢄ-ꢄ ꢄꢎꢄ+]ꢋꢅꢄꢀꢍꢆꢀꢄGꢄꢉꢁ+ꢅꢄ& +ꢅꢄ DFHWDWHꢄꢉꢂꢒꢀꢋꢄDVꢄHOXHQWꢄWRꢄLVRODWHꢄꢆꢍꢆꢀꢀꢄJꢄꢉꢁꢆAꢋꢄRIꢄWULROꢄ
ꢄ ꢄꢎꢄ+]ꢋꢅꢄꢂꢍꢆꢂꢄVꢄꢉꢁ+ꢅꢄ2$FꢋꢅꢄꢂꢍꢆꢈꢄVꢄꢉꢁ+ꢅꢄ2$FꢋꢅꢄꢂꢍꢀꢆꢄVꢄ ;,9ꢅꢄPSꢄꢂꢊꢁ±ꢂꢊꢃƒ&ꢄꢉIURPꢄKH[DQHꢋꢍꢄ,5ꢄVSHFWUXPꢄ
-
ꢉꢁ+ꢅꢄ2$FꢋꢅꢄꢂꢍꢊꢂꢄGꢍGꢄꢉꢀ+ꢅꢄꢀꢌ ꢇ+ꢅꢄ- ꢄ ꢄꢎꢅꢄ- ꢄ ꢄꢀꢎꢄ+]ꢋꢅꢄ ꢉ.%Uꢋꢒꢄ ꢄꢁꢊꢃꢆꢄFP ꢍꢄ +ꢄ105ꢄVSHFWUXPꢄꢉS\ULGLQHꢋꢅꢄ ꢅꢄ
ꢂꢍꢌꢃꢄPꢄꢉꢀ+ꢅꢄꢎ ꢇ+ꢅꢄ- ꢄ ꢄꢀꢃꢄ+]ꢋꢅꢄꢊꢍꢌꢈꢄVHSWꢄꢉꢀ+ꢅꢄꢁꢇ+ꢅꢄꢄ SSPꢒꢄꢆꢍꢎꢊꢄVꢄꢉꢁ+ꢅꢄ& + ꢋꢅꢄꢆꢍꢎꢏꢄVꢄꢉꢁ+ꢅꢄ& + ꢋꢅꢄꢆꢍꢏꢊꢄGꢄ
-
ꢄ ꢄꢃꢍꢂꢄ+]ꢋꢅꢄꢊꢍꢏꢈꢄGꢍGꢄꢉꢀ+ꢅꢄꢂꢂꢇ+ꢅꢄ- ꢄ ꢄꢂꢍꢏꢅꢄ- ꢄ ꢄꢊꢍꢂꢄ+]ꢋꢅꢄ ꢉꢁ+ꢅꢄ& +ꢅꢄ-ꢄ ꢄꢎꢄ+]ꢋꢅꢄꢀꢍꢆꢆꢄGꢄꢉꢁ+ꢅꢄ& +ꢅꢄ-ꢄ ꢄꢎꢄ+]ꢋꢅꢄ
ꢃꢍꢀꢏꢄGꢍGꢄꢉꢀ+ꢅꢄꢂꢁꢇ+ꢅꢄ- ꢄ ꢄꢂꢍꢏꢅꢄ- ꢄ ꢄꢎꢍꢊꢄ+]ꢋꢍꢄ &ꢄ105ꢄ ꢀꢍꢆꢁꢄGꢄꢉꢁ+ꢅꢄ& +ꢅꢄ-ꢄ ꢄꢎꢄ+]ꢋꢅꢄꢀꢍꢁꢆꢄGꢄꢉꢁ+ꢅꢄ& +ꢅꢄ-ꢄ ꢄ
VSHFWUXPꢅꢄ ꢅꢄSSPꢒꢄꢏꢍꢈꢌꢄTꢄꢉ& ꢋꢅꢄꢀꢂꢍꢂꢂꢄTꢄꢉ& ꢋꢅꢄꢀꢂꢍꢈꢈꢄTꢄ ꢌꢍꢊꢄ+]ꢋꢅꢄꢁꢍꢎꢆꢄWꢄꢉꢀ+ꢅꢄꢂꢁꢇ+ꢅꢄ-ꢄ ꢄꢃꢍꢀꢄ+]ꢋꢅꢄꢁꢍꢈꢁꢄVHSWꢄꢉꢀ+ꢅꢄ
ꢁ
ꢀ
ꢇ+ꢅꢄ-ꢄ ꢄꢊꢍꢈꢄ+]ꢋꢅꢄꢊꢍꢆꢊꢄGꢄꢉꢀ+ꢅꢄꢂꢂꢇ+ꢅꢄ-ꢄ ꢄꢁꢍꢂꢄ+]ꢋꢍꢄꢄ
ꢄ105ꢄVSHFWUXPꢄꢉS\ULGLQHꢋꢅꢄ ꢅꢄSSPꢒꢄꢀꢀꢍꢊꢌꢄTꢄꢉ& ꢋꢅꢄ
ꢂꢍꢂꢁꢄTꢄꢉ& ꢋꢅꢄꢀꢂꢍꢃꢌꢄTꢄꢉ& ꢋꢅꢄꢀꢁꢍꢁꢃꢄTꢄꢉ& ꢋꢅꢄꢀꢎꢍꢌꢆꢄTꢄ
ꢉ& ꢋꢅꢄꢀꢊꢍꢏꢏꢄTꢄꢉ& ꢋꢅꢄꢀꢎꢍꢀꢃꢄTꢄꢉ& ꢋꢅꢄꢂꢆꢍꢈꢁꢄWꢄꢉ& ꢋꢅꢄꢂꢀꢍꢂꢆꢄTꢄ
ꢉ&2&+ ꢋꢅꢄꢂꢀꢍꢃꢂꢄTꢄꢉ&2&+ ꢋꢅꢄꢂꢀꢍꢃꢏꢄTꢄꢉ&2&+ ꢋꢅꢄꢄ
ꢂꢀꢍꢎꢈꢄTꢄꢉ& ꢋꢅꢄꢂꢈꢍꢌꢎꢄGꢄꢉ& ꢋꢅꢄꢂꢎꢍꢃꢁꢄWꢄꢉ&ꢋꢅꢄꢂꢈꢍꢂꢂꢄWꢄꢉ&ꢋꢅꢄ
&
ꢉ& ꢋꢅꢄꢂꢀꢍꢌꢂꢄWꢄꢉ& ꢋꢅꢄꢂꢂꢍꢃꢊꢄTꢄꢉ& ꢋꢅꢄꢂꢊꢍꢃꢎꢄWꢄꢉ& ꢋꢅꢄꢂꢎꢍꢁꢀꢄGꢄ
ꢉ& ꢋꢅꢄꢂꢈꢍꢃꢃꢄWꢄꢉ& ꢋꢅꢄꢂꢏꢍꢂꢀꢄWꢄꢉ&ꢋꢅꢄꢁꢂꢍꢊꢀꢄWꢄꢉ&ꢋꢅꢄꢁꢂꢍꢃꢌꢄWꢄ
ꢉ&ꢋꢅꢄꢁꢃꢍꢈꢂꢄGꢄꢉ&ꢋꢅꢄꢁꢃꢍꢈꢆꢄVꢄꢉ& ꢋꢅꢄꢁꢎꢍꢃꢂꢄWꢄꢉ&ꢋꢅꢄꢁꢏꢍꢁꢈꢄWꢄ
ꢉ&ꢋꢅꢄꢊꢆꢍꢃꢃꢄWꢄꢉ& ꢋꢅꢄꢊꢀꢍꢊꢀꢄGꢄꢉ& ꢋꢅꢄꢊꢂꢍꢂꢀꢄGꢄꢉ& ꢋꢅꢄꢊꢂꢍꢎꢌꢄVꢄ
ꢉ& ꢋꢅꢄꢊꢃꢍꢂꢆꢄGꢄꢉ&ꢋꢅꢄꢃꢁꢍꢁꢌꢄGꢄꢉ& ꢋꢅꢄꢃꢊꢍꢌꢁꢄGꢄꢉ&ꢋꢅꢄꢃꢌꢍꢈꢂꢄGꢄ
ꢉ& ꢋꢅꢄꢎꢆꢍꢌꢃꢄGꢄꢉ&ꢋꢅꢄꢎꢂꢍꢃꢁꢄGꢄꢉ& ꢋꢅꢄꢎꢌꢍꢁꢌꢄGꢄꢉ& ꢋꢍꢄꢄ
ꢁ
ꢆꢍꢃꢃꢄWꢄꢉ&ꢋꢅꢄꢁꢂꢍꢆꢀꢄGꢄꢉ&ꢋꢅꢄꢁꢁꢍꢏꢎꢄWꢄꢉ&ꢋꢅꢄꢁꢃꢍꢌꢎꢄVꢄꢉ& ꢋꢅꢄ
ꢌꢍꢈꢁꢄWꢄꢉ&ꢋꢅꢄꢁꢈꢍꢌꢁꢄGꢄꢉ& ꢋꢅꢄꢁꢏꢍꢎꢎꢄWꢄꢉ& ꢋꢅꢄꢊꢆꢍꢁꢌꢄGꢄꢉ& ꢋꢅꢄ
ꢁ
ꢊꢀꢍꢊꢀꢄWꢄꢉ& ꢋꢅꢄꢊꢂꢍꢎꢃꢄVꢄꢉ& ꢋꢅꢄꢊꢊꢍꢎꢁꢄGꢄꢉ&ꢋꢅꢄꢊꢎꢍꢊꢎꢄGꢄꢉ& ꢋꢅꢄ
ꢃꢁꢍꢎꢊꢄGꢄꢉ&ꢋꢅꢄꢌꢃꢍꢂꢌꢄGꢄꢉ& ꢋꢅꢄꢎꢁꢍꢈꢃꢄGꢄꢉ& ꢋꢅꢄꢎꢁꢍꢌꢊꢄGꢄꢉ&ꢋꢅꢄ
ꢎꢂꢍꢈꢃꢄGꢄꢉ& ꢋꢅꢄꢀꢎꢆꢍꢊꢎꢄVꢄꢉ&2&+ꢋꢅꢄꢀꢎꢆꢍꢈꢁꢄVꢄꢉ&2&+ꢋꢅꢄ
ꢀꢎꢆꢍꢈꢈꢄVꢄꢉ&2&+ꢋꢅꢄꢂꢀꢊꢍꢌꢎꢄVꢄꢉ& ꢋꢍꢄ
ꢊꢃꢃ6ꢆꢃꢉ6ꢋꢂꢈꢌꢆꢈꢌꢂ(WK\OHQHGLVXOIDQ\Oꢂꢉ ꢂK\GUR[\ꢂ
HUJRVWDQHꢂꢃꢃꢆꢃꢉꢂGL\OꢀGLDFHWDWHꢀꢊ;9ꢋꢅꢄ)ROORZLQJꢄWKHꢄ
SURFHGXUHꢄGHVFULEHGꢄDERYHꢄIRUꢄWKHꢄV\QWKHVLVꢄRIꢄFRPꢇ
SRXQGꢄ,9ꢅꢄIURPꢀꢆꢍꢆꢂꢆꢄJꢄꢉꢆꢍꢆꢁꢊꢄPPROꢋꢄRIꢄꢀꢃꢇR[Rꢄ
VWHURLGꢄ;ꢄZHꢄREWDLQHGꢄꢆꢍꢆꢀꢂꢄJꢄꢉꢃꢈAꢋꢄRIꢄGLWKLRDFHWDOꢄ
ꢊꢃꢃ5ꢆꢃꢉ5ꢋꢂꢈꢌꢆꢈꢌꢂ(WK\OHQHGLVXOIDQ\Oꢂꢉ ꢂK\GUR[\ꢂ
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VWHURLGꢄ;,ꢄZHꢄREWDLQHGꢄꢆꢍꢆꢃꢆꢄJꢄꢉꢏꢁAꢋꢄRIꢄGLWKLRDFHWDOꢄ
,,ꢄDVꢄDQꢄRLO\ꢄVXEVWDQFHꢍꢄ,5ꢄVSHFWUXPꢄꢉILOPꢋꢅꢄ ꢅꢄFP ꢒꢄ
ꢊꢂꢆꢅꢄꢀꢎꢊꢆꢅꢄꢀꢂꢃꢆꢍꢄ +ꢄ105ꢄVSHFWUXPꢅꢄ ꢅꢄSSPꢒꢄꢆꢍꢎꢂꢄGꢄ
ꢉꢁ+ꢅꢄ& +ꢅꢄ-ꢄ ꢄꢎꢄ+]ꢋꢅꢄꢆꢍꢎꢎꢄVꢄꢉꢁ+ꢅꢄ& +ꢋꢅꢄꢆꢍꢎꢈꢄGꢄDQGꢄ
ꢆꢍꢈꢀꢄGꢄꢉꢌ+ꢅꢄ& + ꢅꢄ& + ꢅꢄ-ꢄ ꢄꢌꢄ+]ꢋꢅꢄꢆꢍꢈꢂꢄVꢄꢉꢁ+ꢅꢄ
+ ꢋꢅꢄꢆꢍꢏꢊꢄGꢄꢉꢁ+ꢅꢄ& + ꢅꢄ-ꢄ ꢄꢌꢄ+]ꢋꢅꢄꢀꢍꢏꢎꢄVꢄꢉꢁ+ꢅꢄ
$FꢋꢅꢄꢀꢍꢏꢈꢄVꢄꢉꢁ+ꢅꢄ2$FꢋꢅꢄꢂꢍꢏꢌꢄGꢍGꢄꢉꢀ+ꢅꢄꢀꢌꢇ+ꢅꢄ- ꢄ ꢄꢏꢅꢄꢄ
ꢄ ꢄꢀꢏꢄ+]ꢋꢅꢄꢁꢍꢀꢆ±ꢁꢍꢁꢎꢄPꢄꢉꢊ+ꢅꢄ6&+ꢋꢅꢄꢁꢍꢃꢁꢄPꢄꢉꢀ+ꢅꢄꢄ
;9ꢄDVꢄDQꢄRLO\ꢄVXEVWDQFHꢍꢄ +ꢄ105ꢄVSHFWUXPꢅꢄ ꢅꢄSSPꢒꢄ
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ꢆꢍꢈꢂꢄVꢄꢉꢁ+ꢅꢄ& + ꢋꢐꢄꢆꢍꢈꢊ±ꢆꢍꢏꢊꢄPꢄꢉꢏ+ꢅꢄ& + ꢅꢄ& +ꢅꢄ
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+ꢅꢄ-ꢄ ꢄꢎꢄ+]ꢋꢐꢄꢂꢍꢆꢌꢄVꢄꢉꢁ+ꢅꢄ2$FꢋꢐꢄꢂꢍꢆꢈꢄVꢄꢉꢁ+ꢅꢄ2$Fꢋꢐꢄ
ꢂꢍꢎꢈꢄGꢍGꢄꢉꢀ+ꢅꢄꢀꢌꢇ+ꢅꢄ- ꢄ ꢄꢎꢅꢄ- ꢄ ꢄꢀꢃꢄ+]ꢋꢐꢄꢁꢍꢆꢈꢄPꢅꢄꢄ
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ꢁ
ꢀ
ꢍꢂꢊꢄPꢅꢄDQGꢄꢁꢍꢊꢂꢄPꢄꢉꢊ+ꢅꢄ6&+ꢋꢅꢄꢁꢍꢌꢄPꢄꢉꢀ+ꢅꢄꢁꢇ+ꢅꢄ- ꢄ ꢄ
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ꢂꢁꢇ+ꢅꢄ- ꢄ ꢄꢁꢅꢄ- ꢄ ꢄꢌꢄ+]ꢋꢍꢄꢄ
ꢁ
ꢇ+ꢅꢄ- ꢄ ꢄꢀꢏꢄ+]ꢋꢅꢄꢃꢍꢆꢆꢄPꢄꢉꢂ+ꢅꢄꢂꢂꢇ+ꢅꢄꢂꢁꢇ+ꢋꢍꢄ
ꢊꢃꢃ6ꢆꢃꢉ6ꢋꢂꢉ ꢂ+\GUR[\HUJRVWDQHꢂꢃꢃꢆꢃꢉꢂGL\Oꢀ
GLDFHWDWHꢀꢊ;9,ꢋꢅꢄ)ROORZLQJꢄWKHꢄSURFHGXUHꢄGHVFULEHGꢄ
DERYHꢄIRUꢄWKHꢄV\QWKHVLVꢄRIꢄFRPSRXQGꢄ9ꢅꢄIURPꢀꢆꢍꢆꢀꢂꢄJꢄ
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